- Factorial design evaluation of the Suzuki cross-coupling reaction using a magnetically recoverable palladium catalyst
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A magnetically recoverable catalyst [Fe3O4@SiO2-AEAPTMS-Pd(II)] was prepared, fully characterized and had its catalytic activity evaluated on the Suzuki cross-coupling reaction under microwave irradiation. The reaction conditions for the synthesis of biaryl compounds was optimized in two stages - an initial fractional design 24, in which the parameters reaction time, temperature, solvent and catalyst loading were evaluated, followed by a Doehlert design. The factorial design proved to be a viable approach for obtaining the optimal reaction conditions based on a relatively small number of experiments. Additionally, the biaryl derivatives synthesized by this method were obtained with good to excellent yields (71–96%) and the recovery and reuse of the palladium catalyst was also evaluated.
- Guerra, Raíza R.G.,Martins, Felipe C.P.,Lima, Carolina G.S.,Gon?alves, Ricardo H.,Leite, Edson R.,Pereira-Filho, Edenir R.,Schwab, Ricardo S.
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- Inorganic–organic hybrid nano magnetic based nickel complex as a novel, efficient and reusable nanocomposite for the synthesis of biphenyl compounds in green condition
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The carbon–carbon cross coupling reactions through transition-metal-catalyzed processes has been significantly developed for their important synthetic applications. A novel and fantastic nickel-based catalyst supported on bis (propyl malononitrile) (NiFe2O4@SiO2-BPMN-Ni) was easily prepared and evaluated as heterogeneous nanocatalyst in Suzuki cross coupling reaction of various aryl halides and phenylboronic acid. The catalyst prepared and characterized by using fourier transform infrared (FT-IR), powder X-ray diffraction (XRD), scanning electron microscopy (SEM), energy-dispersive X-ray spectroscopy (EDX), thermo gravimetric analysis (TGA) and vibrating sample magnetometer (VSM) techniques. Compare to the previous works, this procedure have advantages such as easy workup, high yields of products, environmentally benign and short reaction times. The catalyst can be separated by external magnet and reused six times without any significant loss of activity which is an additional sustainable characteristic of this method. The products have been confirmed by spectroscopic and physical data such as; IR, 1H NMR, and melting point.
- Naeimi, Hossein,Kiani, Fatemeh
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- Ultrasound-assisted synthesis of unsymmetrical biaryls by Stille cross-coupling reactions
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We describe herein an efficient method for the synthesis of unsymmetrically-substituted biphenyls using a sonochemical variation of the Stille coupling, whose results have also been compared with the conventional silent reaction. Ultrasound significantly enhances this useful organometallic transformation affording products in higher yields and in shorter reaction times than non-irradiated reactions. The scope has been explored with a selection of arylstannanes as precursors and, remarkably, no by-products resulting from homo-coupling could be detected.
- Domini, Claudia E.,Silbestri, Gustavo F.,Fernández Band, Beatriz,Chopa, Alicia B.
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- A comparative Suzuki reaction of aryl halides using a new dimeric orthopalladated complex under conventional and microwave irradiation conditions
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The cross-coupling reaction between phenylboronic acid and various types of aryl halides (Suzuki reaction) was carried out using a catalytic amount of a new phosphine-based catalyst under microwave irradiation. The reaction conditions were optimized and results showed that, by application of this catalytic system, N-methyl-2-pyrrolidone as the solvent and potassium carbonate as the base, reactions could be completed in a short reaction time with high to excellent yields. Copyright 2012 John Wiley & Sons, Ltd. The Suzuki reaction of aryl halides was carried out using a new catalyst under the optimized conditions. Application of microwave irradiation lead to very good results in a short time. Copyright
- Hajipour, Abdol R.,Karami, Kazem,Tavakoli, Ghazal
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- Palladium-catalyzed benzene arylation: Incorporation of catalytic pivalic acid as a proton shuttle and a key element in catalyst design
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A palladium-pivalic acid cocatalyst system has been developed that exhibits unprecedented reactivity in direct arylation. This reactivity is illustrated with the first examples of high yielding direct metalation-arylation reactions of a completely unactivated arene, benzene. Experimental and computational evidence indicates that the pivalate anion is a key component in the palladation/C-H bond breaking event, that it lowers the energy of C-H bond cleavage and acts as a catalytic proton shuttle from benzene to the stoichiometric carbonate base. Eight examples of substituted aryl bromides are included which undergo direct arylation with benzene in 55-85% yield Copyright
- Lafrance, Marc,Fagnou, Keith
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- Cubical Palladium Nanoparticles on C@Fe3O4 for Nitro reduction, Suzuki-Miyaura Coupling and Sequential Reactions
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Cubical Pd nanoparticles incorporated magnetically recyclable nanoreactor (Pd cNPs/C@Fe3O4) are found to be efficient catalysts for the hydrogenation or aromatic nitrocompounds, Suzuki-Miyaura coupling and the sequential reaction of [Formula presented] coupling followed by reduction of nitrobiphenyl substrates. A variety of aryl iodides, bromides and chlorides were coupled with phenylboronic acids to form corresponding biaryl products and variety of nitro aromatic compounds was hydrogenated with excellent yield and high TON. The catalytic activity of palladium cubical nanoparticles (Pd cNPs) embedded with excess of {100} surface facets are superior compared to Pd spherical nanoparticles (Pd sNPs) embedded with mixed surface facets. The catalytic efficiency remains unaltered even after five repeated cycles. The observed enhanced catalytic activity is attributed to the high density of low-coordinated Pd {100} atoms present at the surface of the Pd cNPs/C@Fe3O4 catalyst, confirmed by HR-TEM studies. Also, the catalyst is truly heterogeneous, highly stable, does not require any toxic ligands, has wide substrate scope in both nitroreduction and Suzuki-Miyaura coupling reaction along with the ability to catalyse in a sequential manner, magnetically separable from the reaction mixture and can be reused.
- Kumar, Basuvaraj Suresh,Amali, Arlin Jose,Pitchumani, Kasi
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- Ultrasonic accelerated coupling reaction using magnetically recyclable bis (propyl molononitril) Ni complex nanocatalyst: A novel, green and efficient synthesis of biphenyl derivatives
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A novel, green and rapid sonochemical research to preparation of the biphenyls was carried out through the coupling reaction between various aryl halides and phenylboronic acid by using bis(propyl malononitrile) Ni (0) complex (NiFe2O4@SiO2-BPMN-Ni) as an efficient nano catalyst. The catalyst can be recycled via an external magnet and reused several times without considerable loss of its catalytic activity. Compare to the previous works, this procedure has advantages such as easy workup, high yields of products, environmentally benign and short reaction times. The novel nickel catalyst prepared and characterized by FT-IR, XRD, SEM, EDX, TGA and VSM techniques.
- Kiani, Fatemeh,Naeimi, Hossein
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- Suzuki cross-coupling reaction catalyzed by palladium-supported sepiolite
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Palladium-supported sepiolite clay has effectively catalyzed the Suzuki cross-coupling reaction of phenylboronic acid with aryl halide including less reactive electron-rich aryl bromides.
- Shimizu, Ken-Ichi,Kan-No, Toshiki,Kodama, Tatsuya,Hagiwara, Hisahiro,Kitayama, Yoshie
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- Alumina as Solid-State Ligand in Enhancing the Redox Catalytic Property of Iron Oxide Grafted AlSBA-15 towards Arylation of Arene
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2–8 wt % iron has been grafted over SBA-15 and 10 wt % alumina grafted SBA-15 (AlSBA-15) through selective extraction deposition technique using LaFeO3 as iron precursor in acidic solution. DRS-UV spectra confirmed the presence of iron as isolated Fe(III), Fe(III)-clusters and amorphous FeOx oligomers. SEM-EDX mapping, FT-IR, XPS, HR-TEM and 27Al MAS NMR characterisation results confirmed that iron grafted over AlSBA-15 preferentially reside on the alumina. The donor-acceptor interaction of grafted iron ions with alumina atoms displaying Lewis acid properties stabilized iron at higher oxidation state Fe(III+δ). This increased the BE of Fe2p electrons (XPS) and shifted the temperature of iron reduction in 2–8 wt %Fe/AlSBA-15 materials to higher value (600 °C) compared with Fe/SBA-15 (H2-TPR). In arylation of benzene, 8 wt %Fe/AlSBA-15 demonstrated excellent redox catalytic activity with TOF close to homogeneous catalyst and 82 % biphenyl yield. The catalyst demonstrated consistent catalytic performance for 7 cycles.
- Rajendran, Chandran,Thirumoorthy, Kulandaivellu,Satishkumar, Govindaswamy,Landau, Miron V.
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- Direct arylation catalysis with chloro[8-(dimesitylboryl)quinoline-κN]copper(I)
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We report direct arylation of arylhalides with unactivated sp2 C-H bonds in benzene and naphthalene using a copper(I) catalyst featuring an ambiphilic ligand, (quinolin-8-yl)dimesitylborane. Direct arylation could be achieved with 0.2 mol % catalyst and 3 equivalents of base (KO(t-Bu)) at 80 °C to afford TON ≈160-190 over 40 hours.
- Tamang, Sem Raj,Hoefelmeyer, James D.
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- Poly(: O -aminothiophenol)-stabilized Pd nanoparticles as efficient heterogenous catalysts for Suzuki cross-coupling reactions
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Poly(o-aminothiophenol) (PATP)-stabilized Pd nanoparticles with Pd nanoparticles embedded in a polymer matrix have been obtained through a facile one-step route by mixing o-aminothiophenol monomer and Pd(NO3)2 in an acidic aqueous solution without additional template or surfactant. The redox reaction between o-aminothiophenol and Pd(NO3)2 leads to the simultaneous formation of a PATP polymer and Pd nanoparticles. The PATP-stabilized Pd nanoparticles have been characterized by TEM, FTIR, XRD, ICP-MS and XPS. Catalytic results showed that PATP-stabilized Pd nanoparticles were highly stable and active catalysts for Suzuki cross-coupling reactions, where high yields could be achieved with arylboronic acid and aryl halides bearing a variety of substituents.
- Chen, Yuan,Wang, Minggui,Zhang, Long,Liu, Yan,Han, Jie
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- TBAF-assisted palladium-catalyzed Suzuki reaction in water under the ligand and base-free conditions
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Tetrabutyl ammonium fluoride (abbreviated as TBAF)-assisted palladium-catalyzed Suzuki reaction in neat water has been demonstrated under the ligand and base-free conditions. The cross-coupling of aryl or heteroaryl bromides with arylboronic acids generated the corresponding products in good to excellent yields in the presence of low concentration of palladium acetate in combination with TBAF under air.
- Wu, Xiang-Mei,Gu, Yong-Bing
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- Features of polychlorinated biphenyls nitration
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Nitration of mono-, di-, and trichlorobiphenyls has been studied. The nitration degree depends on the number of chlorine substituents; one to four nitro groups can be introduced. The conclusions have been confirmed by results of nitration of the "Trikhlorbifenil" technical mixture of polychlorinated biphenyls.
- Gorbunova,Pervova,Plotnikova,Saloutin,Chupakhin
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- Suzuki coupling catalyzed by chloro({2-[mesityl(quinolin-8-yl-κN)boryl]-3,5-dimethylphenyl}methyl-κC)palladium(II)
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The title compound was evaluated as catalyst for Suzuki coupling of aryl halides (X = I, Br) with phenylboronic acid at room temperature. The rates of the reactions increase with increasing Hammet sigma constant of m-substituents on the arylhalide. The presence of ortho groups on the arylhalides had the effect of lowering the reaction rates. Density functional theory study of the mechanism for the formation of a Pd(0) complex from the title molecule was performed. Reductive elimination of chloride and the η4-BCCC moiety was endergonic and ruled out as a likely pathway. Instead, conversion of the title molecule to phenyl({2-[mesityl(quinolin-8-yl-κN)boryl]-3,5-dimethylphenyl}methyl-κC)palladium(II) complex is thermodynamically favored and predicted to further react with the solvent and the Suzuki coupling reagents to undergo reductive elimination of diphenyl to form a reactive Pd(0) complex.
- Tamang, Sem Raj,Achazi, Andreas J.,Rust, Haley S.,Dhungana, Pramod,Miró, Pere,Hoefelmeyer, James D.
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- Biaryl Coupling of Aryldiazonium Salts and Arylboronic Acids Catalysed by Gold
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A gold-catalysed coupling of aryldiazonium salts with arylboronic acids is described. The reactions proceed in satisfactory yields under irradiation with blue LEDs in the presence of KF and a catalytic amount of ascorbic acid. Notably, 4-nitrobenzendiazonium tetrafluoroborate is sufficiently reactive to undergo the coupling with a variety of arylboronic acids in the absence of aryl radical initiators. The coupling is applicable for electron-donating and electron-withdrawing groups present at the para, ortho, and meta positions of both substrates.
- Medina-Mercado, Ignacio,Porcel, Susana
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- Merging Iridium-Catalyzed C-H Borylations with Palladium-Catalyzed Cross-Couplings Using Triorganoindium Reagents
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A versatile and efficient method to prepare borylated arenes furnished with alkyl, alkenyl, alkynyl, aryl, and heteroaryl functional groups is developed by merging Ir-catalyzed C-H borylations (CHB) with a chemoselective palladium-catalyzed cross-coupling of triorganoindium reagents (Sarandeses-Sestelo coupling) with aryl halides bearing a boronic ester substituent. Using triorganoindium cross-coupling reactions to introduce unsaturated moieties enables the synthesis of borylated arenes that would be difficult to access through the direct application of the CHB methodology. The sequential double catalyzed procedure can be also performed in one vessel.
- Chhabra, Arzoo,Gil-Negrete, José M.,Jayasundara, Chathurika R. K.,Maleczka, Robert E.,Martínez, M. Montserrat,Montero Bastidas, Jose R.,Pérez Sestelo, José,Smith, Milton R.
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- Efficient photocatalytic chemoselective and stereoselective C-C bond formation over AuPd@N-rich carbon nitride
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Heterogeneous chemoselective or stereoselective C-C coupling reactions remain extremely challenging in traditional organic synthesis. Here, we constructed a AuPd@N-rich carbon nitride (NRCN) photocatalyst through simple ammonia solution heat treatment of carbon nitride and then AuPd NP loading. AuPd@NRCN exhibited extraordinary light color promoted catalytic performance in C-C bond formation under visible light in air. Surprisingly, both high chemoselectivity to unsymmetrical Ullmann biaryl products and satisfactory stereoselectivity to Z-type Heck reaction products could be achieved by changing the light source color. Various substrates exhibited great potential for the economical synthesis of unsymmetrical biaryl products and Z-type olefins. Efficient visible light promoted C-I bond activation accompanied with improved photocatalytic coupling reaction efficiency over AuPd@NRCN was verified firstly by in situ DRIFTS. Considering that the Ullmann cross-coupling reaction is a multi-photon reaction, the improved photocatalytic performance in the Ullmann cross-coupling reaction using a combination of light sources with different colors might be due to the activation of different substrates and/or steps requiring different energies, and the combination of the two energy sources was beneficial for improving the activation efficiency of different substrates and/or steps. The activation of iodobenzene and styrene in the Heck reaction with light was also beneficial to the formation of the stilbene product. The light color promoted chemoselectivity and stereoselectivity are expected to have profound impact on organic synthetic methodology improvement. This journal is
- Jiang, Heyan,Xu, Jie,Zhang, Sishi,Cheng, Hongmei,Zang, Cuicui,Bian, Fengxia
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p. 219 - 229
(2021/01/28)
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- Palladium Immobilized on a Polyimide Covalent Organic Framework: An Efficient and Recyclable Heterogeneous Catalyst for the Suzuki–Miyaura Coupling Reaction and Nitroarene Reduction in Water
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An efficient and recyclable Pd nano-catalyst was developed via immobilization of Pd nanoparticles on polyimide linked covalent organic frameworks (PCOFs) that was facilely prepared through condensation of melamine and 3,3′,4,4′-biphenyltetracarboxylic dianhydride. The Pd nanoparticles (Pd NPs) catalyst was thoroughly characterized by FT-IR, XRD, SEM, TEM. Furthermore, the catalytic activity of Pd NPs catalyst was evaluated by Suzuki–Miyaura coupling reaction and nitroarene reduction in water, respectively. The excellent yields of corresponding products revealing revealed that the Pd NPs catalyst could be applied as an efficient and reusable heterogeneous catalyst for above two reactions. Graphical Abstract: [Figure not available: see fulltext.]
- Dong, Zhenhua,Pan, Hongguo,Gao, Pengwei,Xiao, Yongmei,Fan, Lulu,Chen, Jing,Wang, Wentao
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- Buchwald ligand-assisted Suzuki cross-coupling of polychlorobenzenes
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Screening of four Buchwald ligands for the cross-coupling of isomeric di-, tri- and tetrachlorobenzenes with arylboronic acids revealed that good yields of exhaustive substitution can be best provided by 2-dicyclohexylphosphino-2′-(dimethylamino) biphenyl (DavePHOS).
- Burukin, Alexander S.,Vasil'ev, Andrei A.,Zhdankina, Galina M.,Zlotin, Sergei G.
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p. 400 - 402
(2021/06/07)
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- Preparation and characterization of cellulose sulfate/Pd nanocatalsysts with remarkable efficiency for Suzuki–Miyaura reaction
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Heterogeneous catalysis with noble metal NPs are quite attractive due to unique surface chemistry and tuneable physicochemical properties. In this work, an efficient and simple method was used to synthesize palladium nanoparticles supported on cellulose sulfate. The resulted composites were characterized using various techniques such as X-ray powder diffraction (XRD), FT-IR, energy dispersive X-ray spectroscopy (EDS), scanning electron microscopy (SEM), transmission electron microscopy (TEM), and thermogravimetric analysis (TGA) to verify the chemical structure and morphological properties of nanocatalysts. Next, the synthesized catalyst was utilized in Suzuki–Miyaura reaction between aryl bronic acid and different aryl halides. The catalysis reaction was carried out under atmospheric pressure where high efficiency, unique and simple work-up procedure as well as excellent yields were achieved.
- Jokar, Mitra,Naeimi, Hossein,Nabi Bidhendi, Gholamreza
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- Construction of Bulky Ligand Libraries by Ru(II)-Catalyzed P(III)-Assisted ortho-C-H Secondary Alkylation
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Modification of commercially available biaryl monophosphine ligands via ruthenium(II)-catalyzed P(III)-directed-catalyzed ortho C-H secondary alkylation is described. The use of highly ring-strained norbornene as a secondary alkylating reagent is the key to this transformation. A series of highly bulky ligands with a norbornyl group were obtained in excellent yields. The modified ligands with secondary alkyl group outperformed common substituted phosphines in the Suzuki-Miyaura cross-coupling reaction at a ppm mole level of Pd catalyst.
- Li, Jia-Wei,Li, Ming,Liu, Yue-Jin,Tao, Jun-Yang,Wang, Liang-Neng,Zeng, Ming-Hua
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supporting information
p. 11915 - 11925
(2021/09/13)
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- A Next-Generation Air-Stable Palladium(I) Dimer Enables Olefin Migration and Selective C?C Coupling in Air
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We report a new air-stable PdI dimer, [Pd(μ-I)(PCy2tBu)]2, which triggers E-selective olefin migration to enamides and styrene derivatives in the presence of multiple functional groups and with complete tolerance of air. The same dimer also triggers extremely rapid C?C coupling (alkylation and arylation) at room temperature in a modular and triply selective fashion of aromatic C?Br, C?OTf/OFs, and C?Cl bonds in poly(pseudo)halogenated arenes, displaying superior activity over previous PdI dimer generations for substrates that bear substituents ortho to C?OTf.
- Kundu, Gourab,Rissanen, Kari,Schoenebeck, Franziska,Sperger, Theresa
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supporting information
p. 21930 - 21934
(2020/10/02)
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- Transition-Metal-Free Oxidative Cross-Coupling of Tetraarylborates to Biaryls Using Organic Oxidants
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Readily prepared tetraarylborates undergo selective (cross)-coupling through oxidation with Bobbitt's salt to give symmetric and unsymmetric biaryls. The organic oxoammonium salt can be used either as a stoichiometric oxidant or as a catalyst in combination with in situ generated NO2 and molecular oxygen as the terminal oxidant. For selected cases, oxidative coupling is also possible with NO2/O2 without any additional nitroxide-based cocatalyst. Transition-metal-free catalytic oxidative ligand cross-coupling of tetraarylborates is unprecedented and the introduced method provides access to various biaryl and heterobiaryl systems.
- Gerleve, Carolin,Studer, Armido
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p. 15468 - 15473
(2020/05/06)
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- Palladium Ion Catalysed Oxidative C–C Bond Formation Reactions in Arylboronic Acid: Application of Cordierite Monolith Coated Catalyst
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Abstract: Catalytic efficiency of palladium ion substituted in TiO2, Ti0.97Pd0.03O1.97 is successfully exploited for the oxidative homocoupling of arylboronic acid and oxidative Heck coupling reactions between arylboronic acid and olefins. The reaction protocol provides direct approach to synthesize biphenyls and cinnamates from moderate to good yield with good functional group tolerance. As a result, 11 symmetrical biaryls and 14 cinnamates were synthesized from readily available arylboronic acids. Ti0.97Pd0.03O1.97 powder catalyst is synthesized by solution combustion method and characterized by powder X-ray diffraction. The C–C bond formation reactions were carried out by catalyst cartridge method using Ti0.97Pd0.03O1.97 catalyst coated cordierite monolith. Coating of the catalyst on a cordierite monolith enhanced the applicability of the catalyst and made handling and recycling of the catalyst very easy. Catalyst was recovered and recycled for eight times in both homocoupling and oxidative Heck coupling reactions. The turnover number for both the reactions found to be 443 and 424, respectively. Graphic Abstract: [Figure not available: see fulltext.].
- Bhat, Shrikanth K.,Prasanna,Dasappa, Jagadeesh Prasad,Hegde
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p. 2911 - 2927
(2020/03/31)
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- Dichloroimidazolidinedione-activated one-pot Suzuki–Miyaura cross-coupling of phenols
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The first general method for the Suzuki-type cross-coupling of phenols with aryl boronic acids using dichloroimidazolidinedione (DCID) as a new reagent is presented. In the presence of DCID and Pd/metal–organic framework (MOF), coupling of aryl boronic acids with a wide range of phenols, was carried out smoothly in tetrahydrofuran (THF) at reflux conditions to afford the cross-coupling products in good to excellent yields. The structures of all compounds were corroborated by 1H- and 13C-NMR. A plausible mechanism for this type of reaction is proposed.
- Madankar, Kamelia,Mokhtari, Javad,Mirjafary, Zohreh
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- Organocatalyst in Direct C(sp2)-H Arylation of Unactivated Arenes: [1-(2-Hydroxyethyl)-piperazine]-Catalyzed Inter-/Intra-molecular C-H Bond Activation
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This article describes the identification of 1-(2-hydroxyethyl)-piperazine as a new, cost-effective, highly efficient organocatalyst, which promotes both inter- A nd intra-molecular direct C(sp2)-H arylations of unactivated arenes in the presence of potassium tert-butoxide. While the inter-molecular C-H arylation of unactivated benzenes with aryl halides (Ar-X; X = I, Br, Cl) toward biaryl syntheses underwent smoothly in the presence of only 10 mol percent organocatalyst, the intra-molecular C-H arylation catalytic system composed of 40 mol percent each of the catalyst and the additive (4-dimethylaminopyridine (DMAP)). The novel catalyst was also able to perform both inter- A nd intra-molecular direct arylations simultaneously in a single pot. The mechanistic studies confirmed the involvement of aryl radical anions and proceeded via a single-electron-transfer (SET) mechanism. The large substrate scope, high functional group tolerance, competition experiments, gram-scale synthesis, and kinetic studies further highlight the importance and versatile nature of the methodology as well as the compatibility of the new catalyst. To the best of our knowledge, this is the first report on any organocatalyst that reported detailed investigations of both inter- A nd intra-molecular direct C(sp2)-H arylations of unactivated arenes in a single representation.
- Yadav, Lalit,Tiwari, Mohit K.,Shyamlal, Bharti Rajesh Kumar,Chaudhary, Sandeep
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p. 8121 - 8141
(2020/07/16)
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- Visible-Light-Promoted, Catalyst-Free Gomberg-Bachmann Reaction: Synthesis of Biaryls
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Biaryls were synthesized via a novel visible-light-promoted Gomberg-Bachmann reaction that does not require a photosensitizer or any metal reagents. The formation of an electron donor-acceptor complex between aryl diazonium salts and pyridine allows, under visible-light irradiation, the synthesis of biaryls in moderate-to-high yields.
- Lee, Juyoung,Hong, Boseok,Lee, Anna
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p. 9297 - 9306
(2019/08/12)
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- Uncatalyzed Hydrodechlorination of Dichlorobiphenyls
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Mono-, di-, and trichlorobiphenyls showed different reactivities toward alkali in 2-aminoethanol under reflux: 3-chlorobiphenyl remained unchanged, 2,4,5- and 2,4′,5-trichlorobiphenyls were completely converted to hydroxy derivatives, whereas 3,4-dichlorobiphenyl and a mixture of 2,4′-, 3,4′-, and 4,4′-dichlorobiphenyls gave rise to chlorobiphenyls in addition to hydroxybiphenyls.
- Gorbunova,Pervova,Saloutin,Chupakhin
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p. 988 - 990
(2019/09/03)
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- Murahashi Cross-Coupling at ?78 °C: A One-Pot Procedure for Sequential C?C/C?C, C?C/C?N, and C?C/C?S Cross-Coupling of Bromo-Chloro-Arenes
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The coupling of organolithium reagents, including strongly hindered examples, at cryogenic temperatures (as low as ?78 °C) has been achieved with high-reactivity Pd-NHC catalysts. A temperature-dependent chemoselectivity trigger has been developed for the selective coupling of aryl bromides in the presence of chlorides. Building on this, a one-pot, sequential coupling strategy is presented for the rapid construction of advanced building blocks. Importantly, one-shot addition of alkyllithium compounds to Pd cross-coupling reactions has been achieved, eliminating the need for slow addition by syringe pump.
- Sinha, Narayan,Heijnen, Dorus,Feringa, Ben L.,Organ, Michael G.
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supporting information
p. 9180 - 9184
(2019/07/04)
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- Arylzinc Halides by Silver Catalyzed Zinc Insertion into Aryl Iodides
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A catalytic amount of silver acetate efficiently promotes direct insertion of zinc metal into aryl iodides, having different structure, in ethereal solvent. Electron-rich substrates also rapidly undergo oxidative metalation. The arylzinc iodides formed give Negishi coupling products under mild reaction conditions to obtain biaryls in high yields. Sensitive functional groups like aldehydes and primary amides are well-tolerated.
- Casotti, Gianluca,Iuliano, Anna,Carpita, Adriano
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p. 1021 - 1026
(2019/01/04)
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- N,S-chelating triazole-thioether ligand for highly efficient palladium-catalyzed Suzuki reaction
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1,2,3-Triazole-thioether compounds could serve as efficient ligands for Pd-catalyzed Suzuki reactions of various aryl iodides, bromides and chlorides. The reactions feature wide substrate scope and mild reaction conditions. Besides, shorter reaction time, lower catalyst loadings and quantitative yields with a turnover-frequency (TOF) value of up to 11,880 h?1 are other advantageous of this attractive protocol. The crystal structure analyses and computational studies revealed that the higher catalytic activity of the corresponding chelated palladium complex ascribed to the lower energy gap and the lower redox potential.
- Yan, Qiong,Zheng, Lei,Li, Miaomiao,Chen, Yunfeng
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p. 101 - 105
(2019/07/19)
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- Salicylaldehyde-stabilized palladium nanoparticles for highly efficient suzuki-miyaura reaction at room temperature
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Pd-catalyzed Suzuki-Miyaura cross-coupling reactions promoted by simple and commercial salicylaldehyde-based ligands were investigated. The effect of the ligands was evaluated and the reaction conditions were optimized. Moreover, the physical nature of the palladium was determined by TEM analysis and poison tests. It demonstrated that this catalytic system can be reused for ten consecutive runs and showed excellent activities toward aryl bromides with arylboronic acids at room temperature in air.
- Zhou, Zhen,Cao, Gao,Liu, Ning
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supporting information
p. 547 - 550
(2019/06/11)
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- Pd embedded N, S co-doped graphene wrapped core-shell magnetic nanospheres: Engineered stable nanocatalyst for Suzuki couplings
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Designed nitrogen and sulfur co-doped graphene wrapped magnetic core-shell supported Pd nanoparticles were synthesized through the following steps. Firstly, Fe3O4 was prepared, coated with silica and then functionalized with amine groups to create a positive charge on the structure for enhancing the interaction of the Fe3O4@SiO2 with graphene oxide. Secondary, the pre-catalyst wrapped with graphene to enhance adsorption of aromatic substrates through π–π stacking. Thirdly, graphene was doped with nitrogen and sulfur to increase the grafting of Pd in hybrid. Finally, Pd NPs were attached on the surface of pre-engineered structure to produce Fe3O4@SiO2@N,S-wG@Pd which exhibited high performance in Suzuki reactions. This superior activity can be indexed to the incorporation of N and S atoms into graphene led to high anchoring and well-dispersion of Pd NPs on the nanocomposite surface offering large amounts of active centers, that strongly increased the interaction between Pd and substrates to decreases Pd leaching.
- Rohani, Sahar,Mohammadi Ziarani, Ghodsi,Badiei, Alireza
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- Magnetically recoverable graphene oxide supported Co@Fe3O4/L-dopa for C-C cross-coupling and oxidation reactions in aqueous medium
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We report the synthesis of inexpensive and environmentally benign cobalt(0) nanoparticles on L-3,4-dihydroxyphenylalanine (L-dopa) functionalized and magnetite (Fe3O4) grafted graphene oxide (Co@GO/Fe3O4/L-dopa) which was fully characterized with different techniques such as Scanning Electron Microscopy (SEM), High Resolution Transmission Electron Microscopy (HR-TEM), X-Ray Photoelectron Spectroscopy (XPS), X-ray Powder Diffraction (XRD), Thermogravimetric analysis (TGA), Fourier Transform Infrared Spectroscopy (FTIR), Vibrating Sample Magnetometer (VSM), Carbon Hydrogen Nitrogen (CHN) analysis, Energy Dispersive X-ray (EDX) and Inductively Coupled Plasma Atomic Emission Spectroscopy (ICP-AES). Graphene oxide was used as the core material due to its mechanical, electrical and thermal properties. In order to avoid the cumbersome process of separation, magnetite nanoparticles were coated over the graphene oxide. After the successful preparation of graphene oxide based magnetic nanoparticles, L-dopa was grafted over Fe3O4 nanoparticles so as to provide firm anchoring agent for cobalt nanoparticles. Finally, cobalt(0) nanoparticles were immobilized on the developed magnetic support. The catalytic efficiency of the synthesized catalyst was tested for Suzuki cross-coupling and oxidation reactions, usually carried out by precious and expensive second and third row transition metals; products were obtained in good to excellent yields. The synthesized catalyst represents an attractive alternative to conventional catalysts for Suzuki cross-coupling and oxidation reactions, and is recyclable up to five runs.
- Sharma, Harsha,Sharma, Shally,Sharma, Chandan,Paul, Satya,Clark, James H.
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- Diamines as interparticle linkers for silica-titania supported PdCu bimetallic nanoparticles in Chan-Lam and Suzuki cross-coupling reactions
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A series of highly efficient amine functionalized SiO2-TiO2 supported bimetallic PdCu catalysts with varied metal composition have been synthesized. Ethane-1,2-diamine, butane-1,4-diamine and hexane-1,6-diamine were employed as interparticle linkers for amine functionalization of a SiO2-TiO2 support material so as to study the effect of pendant chain length on stabilization and immobilization of bimetallic nanoparticles. The shortest carbon chain length on the support provided the best results, which may be due to the trapping of metal nanoparticles more efficiently by the basic nitrogen sites. The catalytic activities of these materials were evaluated for C-N and C-C coupling reactions. The most active catalyst, Pd1Cu1@12DA-STS, was characterized by various techniques including SEM, HR-TEM, ICP-AES, XRD, FTIR, EDX, CHN analysis and TGA studies. Moreover, the synthesized catalyst was found to be recyclable for up to five runs without significant loss of activity.
- Jamwal, Babita,Kaur, Manpreet,Sharma, Harsha,Khajuria, Chhavi,Paul, Satya,Clark
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p. 4919 - 4928
(2019/03/26)
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- Modular Functionalization of Arenes in a Triply Selective Sequence: Rapid C(sp2) and C(sp3) Coupling of C?Br, C?OTf, and C?Cl Bonds Enabled by a Single Palladium(I) Dimer
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Full control over multiple competing coupling sites would enable straightforward access to densely functionalized compound libraries. Historically, the site selection in Pd0-catalyzed functionalizations of poly(pseudo)halogenated arenes has been unpredictable, being dependent on the employed catalyst, the reaction conditions, and the substrate itself. Building on our previous report of C?Br-selective functionalization in the presence of C?OTf and C?Cl bonds, we herein complete the sequence and demonstrate the first general arylations and alkylations of C?OTf bonds (in I dimer. This allowed the realization of the first general and triply selective sequential C?C coupling (in 2D and 3D space) of C?Br followed by C?OTf and then C?Cl bonds.
- Keaveney, Sinead T.,Kundu, Gourab,Schoenebeck, Franziska
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supporting information
p. 12573 - 12577
(2018/09/18)
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- Denitrogenative palladium-catalyzed coupling of aryl halides with arylhydrazines under mild conditions
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The development of a method for the Pd(ii)-catalyzed denitrogenative coupling of arylhydrazines to give functionalized biaryls in good yield, using aryl bromides or aryl iodides as convenient and inexpensive aryl sources, is reported. High functional group tolerance is demonstrated for electronically distinct arylhydrazines as well as aryl halides. The desired products were isolated in good to excellent yields for 58 examples. Control experiments and mechanism studies revealed that the transformation undergoes a base-promoted Pd-catalyzed process.
- Chang, Sheng,Dong, Lin Lin,Song, Hai Qing,Feng, Bo
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supporting information
p. 3282 - 3288
(2018/05/15)
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- Direct Aryl-Aryl Coupling without Pre-Functionalization Enabled by Excessive Oxidation of Two-Electron Ag(I)/Ag(III) Catalyst
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Reported herein is a catalytic platform for formation of unsymmetrical biaryls by the coupling between inert Csp2?CH3 and Csp2?H via a tandem catalytic strategy. The platform utilizes traditional AgNO3 catalyst and excess amount of K2S2O8 oxidant. The excessive oxidant present converts the traditional one-electron Ag(I)/Ag(II) chemistry to two-electron Ag(I)/Ag(III) one, enabling one-pot synthesis of aryl-aryl scaffolds by using unactivated cheap commodity chemicals. (Figure presented.).
- Singh, Ajay K.,Kim, Min-Gyu,Lee, Hyune-Jea,Singh, Rakhi,Cho, Seung Hwan,Kim, Dong-Pyo
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supporting information
p. 2032 - 2042
(2018/04/11)
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- Palladium-scavenging self-assembled hybrid hydrogels-reusable highly-active green catalysts for Suzuki-Miyaura cross-coupling reactions
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A hybrid hydrogel based on 1,3:2,4-dibenzylidene sorbitol (DBS) modified with acyl hydrazides combined with agarose was used for in situ reduction and binding of palladium from aqueous mixtures without the need for an external reducing agent. Palladium uptake was monitored and the formation of Pd nanoparticles (PdNPs) trapped within the gel and located close to the nanofibres was confirmed. This gel effectively scavenges palladium from solution to concentrations 10 times). Reactions were purified by simple washing protocols, and leaching of Pd from the gels is limited (1 ppm). The gels were also used in flow-through mode, giving efficient, rapid reactions, with easy work-up. These catalytic gels combine advantages of homogeneous and heterogeneous catalysts-they are solvent compatible with the reaction taking place in a solution-like environment, while the solid-like gel network enables catalyst recycling. In summary, these hydrogels scavenge 'waste' palladium and convert it into gel 'wealth' capable of efficient, environmentally-friendly Suzuki-Miyaura catalysis.
- Slavík, Petr,Kurka, Dustin W.,Smith, David K.
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p. 8673 - 8681
(2018/12/10)
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- Mono-arylation method of dichlorobenzene compounds
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A mono-arylation method of dichlorobenzene compounds comprises the steps as follows: dichlorobenzene compounds shown in formula (I), arylboronic acid shown in formula (2), a N-heterocyclic carbene-palladium complex catalyst, an alkaline substance and a reaction solvent are mixed to react at 0-100 DEG C for 1-24 h under the protection of nitrogen, a reaction solution is subjected to posttreatment,and a mono-arylation product shown in formula (3) is obtained. A novel catalytic system is developed, the catalyst is stable and easy to obtain, the stable and cheap dichlorobenzene compounds can be subjected to the selective mono-arylation reaction, and the method has multiple advantages that the reaction operation is simple, the cost is low, the product is high in yield and purity and the like,is a brand-new method for synthesizing chloro-biphenyl compounds, provides a new synthesis route for the compounds and has good research value and industrial application prospects.
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Paragraph 0024; 0026; 0028; 0029
(2018/05/16)
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- Rapid “Mix-and-Stir” Preparation of Well-Defined Palladium on Carbon Catalysts for Efficient Practical Use
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A facile direct deposition approach for the preparation of recyclable Pd/C catalysts simply by stirring a solution of tris(dibenzylideneacetone)dipalladium(0) with a suitable carbon material was evaluated. An extraordinarily rapid catalyst preparation procedure (0 centers onto the highly accessible surface area and the avoidance of ill-defined PdII/Pd0 states.
- Yakukhnov, Sergey A.,Pentsak, Evgeniy O.,Galkin, Konstantin I.,Mironenko, Roman M.,Drozdov, Vladimir A.,Likholobov, Vladimir A.,Ananikov, Valentine P.
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p. 1869 - 1873
(2018/04/30)
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- Highly active and reusable hydrotalcite-supported Pd(0) catalyst for Suzuki coupling reactions of aryl bromides and chlorides
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A palladium(0) nanocluster supported on hydrotalcite has been prepared and tested for the Suzuki coupling reaction. The prepared catalyst showed very efficient catalytic activity for cross coupling of iodo- and bromoarenes under very mild reaction conditions, affording >90% yield. Under the optimized reaction conditions, chloroarenenes also showed very good reactivity. Transmission electron microscopic imaging data showed the formation of very small Pd(0)-nanoclusters (d = 2.2 ± 0.5 nm) well dispersed on the support, which enhanced the activity and stability of the catalyst for the Suzuki cross-coupling reaction. This catalytic system offers an easy method of preparation with good activity and reusability up to five cycles.
- Karanjit, Sangita,Kashihara, Masaya,Nakayama, Atsushi,Shrestha, Lok Kumar,Ariga, Katsuhiko,Namba, Kosuke
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supporting information
p. 948 - 954
(2018/01/27)
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- Imidazolium-based ionic liquid functionalized reduced graphene oxide supported palladium as a reusable catalyst for Suzuki-Miyaura reactions
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A novel palladium immobilized on reduced graphene oxide heterogeneous catalyst was prepared. The reduced graphene oxide was functionalized by imidazolium-based ionic liquids containing polyethylene glycol monomethyl ether moieties. The prepared catalyst can achieve Suzuki-Miyaura reactions efficiently in green solvents under mild conditions and could be recycled for five catalytic runs without the loss of activity.
- Shi, Xin,Cai, Chun
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supporting information
p. 2364 - 2367
(2018/02/19)
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- Method for preparing biaryl from aryl hydrazine and aryl bromide
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The invention discloses a method for preparing biaryl from aryl hydrazine and aryl bromide. The method comprises the following steps: under the action of a divalent palladium catalyst and a ligand, aryl hydrazine and aryl bromide are subjected to a denitrification coupling reaction in an organic solvent, and after the reaction is ended, the reaction product is subjected to aftertreatment to obtainthe biaryl. In the preparation method, cheap and easily available aryl bromide is used as an aryl source, and the reaction of aryl hydrazine and aryl bromide shows good functional group tolerance, and promotes the palladium catalytic process by alkali.
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Paragraph 0035; 0036; 0037; 0039
(2018/09/21)
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- Transition-Metal-Free C-H Arylation of Unactivated Arenes with 8-Hydroxyquinoline as a Promoter
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A method for the transition-metal-free direct C-H arylation of unactivated arenes is developed with aryl bromides as substrates and 8-hydroxyquinoline as an efficient promoter. A variety of biaryl compounds with structural diversity are obtained in moderate to high yields. Mechanistic studies reveal that the reaction proceeds via a homolytic aromatic substitution pathway.
- Zheng, Xuehua,Wu, Xu-Nian,Chen, Jing-Yi,Luo, Hai-Bin,Wu, Deyan,Wu, Yinuo
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p. 1721 - 1727
(2018/02/06)
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- A Sustainable Heterogeneous Iron Catalyst Fe/SBA-15 towards Direct Arylation of Unactivated C(sp3)?H and C(sp2)?H Bonds with Arenes
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Iron grafted over mesoporous silica (8 wt %Fe/SBA-15) is a sustainable, efficient heterogeneous iron catalyst for direct arylation of biphenyl methane C(sp3)?H and benzene C(sp2)?H bonds. The selective extraction deposition (SED) technique was adopted to graft iron easily over the mesoporous support SBA-15 by using LaFeO3 as an iron precursor. The synthesized catalyst has been characterized by EPR spectroscopy, diffuse reflectance UV/Vis spectroscopy, and temperature programmed reduction (TPR) analysis to understand the coordination environment and state of oxidic iron species grafted over the mesoporous SBA-15. TPR results confirm the presence of isolated, clustered, oligomeric oxidic iron species in the catalyst. The adopted SED technique is highly successful for grafting 8 wt % iron into the mesopores of SBA-15 without forming iron oxide particles. Unlike homogeneous iron, the 8 wt %Fe/SBA-15 catalyst does not need support from an electron-withdrawing group and additives to carry out arylation of benzene and could be successfully recycled five times.
- Rajendran,Satishkumar
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p. 1284 - 1291
(2017/04/14)
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- Direct arylation of inactivated benzene with aryl acyl peroxides toward biaryls
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A direct arylation of inactivated benzene with acyl peroxides was developed, affording biaryls in good to excellent yields. This transformation underwent a radical pathway under metal-free, base-free and additive-free conditions with good functional group compatibility.
- Pan, Changduo,Zhu, Jiawei,Chen, Rongzhen,Yu, Jin-Tao
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supporting information
p. 6467 - 6469
(2017/08/16)
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- ONE STEP DIRECT ARYLATION OF COMMODITY CHEMICALS TO SPECIALTY CHEMICALS BY TANDEM CATALYTIC PLATFORM
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The present invention relates to a continuous direct arylation process based on a tandem catalyst for synthesizing specialty chemicals. A method for synthesizing an aryl-aryl structure from a substrate selected from the group consisting of benzyl alcohol, benzyl amine and toluene which are low value added compounds is developed using a silver ion-containing tandem catalyst. The method is applied for synthesizing hexaphenyl arylene and can be applied for synthesizing high value added compounds (not only natural substances and chemical compounds but pharmaceutical and agricultural pesticide relative fields) directly from primary raw materials through the reaction.COPYRIGHT KIPO 2017
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Paragraph 0038; 0039; 0041; 0042; 0106
(2018/02/28)
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- Salicylic Acid-Catalyzed One-Pot Hydrodeamination of Aromatic Amines by tert-Butyl Nitrite in Tetrahydrofuran
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A significant acceleration in the hydrodeamination of in situ formed diazonium salts (from aromatic amines) has been observed in the presence of 10-mol% salicylic acid, using tetrahydrofuran as the hydrogen donor. The reaction proceeds efficiently at 20 °C for a wide range of substituted anilines, even at 10-mmol scale, without any other additive. The same protocol has been adapted to the selective deuterodeamination of some aromatic amines. Control experiments clearly show that aryl radicals are involved in the reaction mechanism. (Figure presented.).
- Felipe-Blanco, Diego,Alonso, Francisco,Gonzalez-Gomez, Jose C.
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supporting information
p. 2857 - 2863
(2017/08/23)
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- Desulfinylative Pd-catalyzed coupling reaction of arenediazonium salt with aryl sulfinates to give unsymmetrical biaryls
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An efficient route for the synthesis of unsymmetrical biaryls was developed via palladium catalyzed reaction of arenediazonium salts and aryl sulfinates under inert atmosphere. This synthesis involves cascade processes. Tetrabutylammonium iodide was used as an iodide source for in situ formation of aryl iodide, followed by desulfinylative cross-coupling reaction between aryl sulfinates and aryl iodides. A wide range of biaryls were selectively prepared in one pot from simple substrates in good to excellent yields.
- Gund, Sitaram Haribhau,Balsane, Kishor Eknath,Nagarkar, Jayashree Milind
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supporting information
p. 2936 - 2939
(2017/07/11)
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- Manganese-Catalyzed Aerobic Heterocoupling of Aryl Grignard Reagents
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An improved protocol has been developed for the MnCl2-catalyzed cross-coupling reaction of two arylmagnesium bromides under dioxygen. The reaction was achieved by using the Grignard reagents in a 2:1 ratio and 20 % of MnCl2. Very good yields of the heterocoupling product were obtained when the limiting Grignard reagent underwent little homocoupling under the reaction conditions. Arylmagnesium bromides that contain p-methoxy, p-(dimethylamino), p-fluoro, and p-chloro substituents were shown to afford high product yields in the cross-coupling reactions with a variety of substituted aryl Grignard reagents. Heterocyclic Grignard reagents, on the other hand, were less effective substrates for this transformation because of the rapid homocoupling of these reagents under the reaction conditions.
- Ghaleshahi, Hajar Golshahi,Antonacci, Giuseppe,Madsen, Robert
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p. 1331 - 1336
(2017/03/23)
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- Extended Study of Visible-Light-Induced Photocatalytic [4 + 2] Benzannulation: Synthesis of Polycyclic (Hetero)Aromatics
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Herein we report an extended study of [4 + 2] benzannulation reactions of 2-(hetero)aryl-substituted anilines with alkynes by visible light photocatalysis. The method requires the use of tBuONO as a diazotizing agent and 0.3 mol % of fac-Ir(ppy)3 as a photocatalyst at room temperature. The reaction proceeded in a chemo- and regioselective manner with high functional group tolerance under mild conditions allowing the preparation of a wide variety of polycyclic (hetero)aromatic compounds, including phenanthrenes, in moderate to high yields. This procedure is amenable to gram-scale synthesis of 9-phenylphenanthrene.
- Chatterjee, Tanmay,Lee, Da Seul,Cho, Eun Jin
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p. 4369 - 4378
(2017/04/28)
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- Palladium catalyzed desulfinylative couplings between aryl sulfinates and aryl bromide/iodide for the synthesis of biaryls
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We have synthesized biaryls from the coupling reaction between aryl sulfinates and aryl halides using homogeneous palladium catalytic system. The developed method is simple and efficient. These methodologies are particularly useful to prepare symmetrical as well as unsymmetrical biaryls with excellent product yield. The suggested protocol demonstrated a broad substrate scope.
- Gund, Sitaram Haribhau,Balsane, Kishor Eknath,Nagarkar, Jayashree Milind
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p. 5051 - 5056
(2016/07/25)
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- Newly-generated Al(OH)3-supported Pd nanoparticles-catalyzed Stille and Kumada coupling reactions of diazonium salts, (Het)aryl chlorides
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A ligand-free Pd/Al(OH)3 nano-catalyst which is prepared by one-pot three-component method using Pd(PPh3)4, tetra (ethylene glycol), and aluminum tri-sec-butoxide exhibits excellent catalytic activity in Stille cross-couplings of (Het)aryl chlorides, arenediazonium tetrafluoroborate salts with phenyltributylstannane, respectively, and Kumada couplings of (Het)aryl chlorides with various Grignard reagents. More importantly, these two processes show excellent functional group compatibility with moderate to good yields and they are also versatile with respect to not only (Het)aryl chlorides, but also diazonium salts, and heteroaryl Grignard reagents. The nano-catalyst could also be recycled and reused 5 times without loss of activity and decrease of yield.
- Li, Xing,Zhu, Tingting,Shao, Zhongqi,Li, Yingjun,Chang, Honghong,Gao, Wenchao,Zhang, Yongli,Wei, Wenlong
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supporting information
p. 69 - 75
(2015/12/23)
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- Development of a sulfur-modified glass-supported Pd nanoparticle catalyst for Suzuki-Miyaura coupling
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A safe, facile and low-leaching (up to 0.17 ppm) sulfur-modified glass-supported palladium nanoparticle catalyst has been developed for the Suzuki-Miyaura coupling of aryl halides with aryl boronic acids. Most notably, this catalyst was highly recyclable and could be used up to 10 times without any discernible decrease in its activity.
- Xiao, Mincen,Hoshiya, Naoyuki,Fujiki, Katsumasa,Honma, Tetsuo,Tamenori, Yusuke,Shuto, Satoshi,Fujioka, Hiromichi,Arisawa, Mitsuhiro
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p. 1154 - 1160
(2016/08/11)
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- Nicotine functionalized-silica palladium (II) complex: a highly efficient, environmentally benign and recyclable nanocatalyst for C-C bond forming reactions under mild conditions
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An environmentally friendly silica-grafted nicotine-based palladium(II) complex was successfully prepared and evaluated for the first time as novel and efficient nanocatalyst in C-C bond forming reactions. Grafted-nicotine in this catalytic system plays an important role, and as an effective ligand and a quaternary ammonium salt demonstrates an efficient stabilizing effect on the Pd(II) species by a synergistic effect of coordination and electrostatic interactions. The catalyst was well characterized by FT-IR, CHN, XRD, TEM, SEM–EDX, ICP and TG analysis, and demonstrated a highly efficient catalytic activity in the reaction system under phosphine-free and low Pd loading conditions, and the coupled products were produced in good to excellent yields. Furthermore, the catalyst can be easily recovered and reused without a significant loss of activity. Copyright
- Hajipour, Abdol R.,Tadayoni, Nayereh S.,Mohammadsaleh, Fatemeh
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p. 777 - 782
(2016/09/04)
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- Magnetic iron oxide nanoparticles–N-heterocyclic carbene–palladium(II): a new, efficient and robust recyclable catalyst for Mizoroki–Heck and Suzuki–Miyaura coupling reactions
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A new and efficient nanoparticle–N-heterocyclic carbene–palladium complex was synthesized and characterized using Fourier transform infrared spectroscopy, thermogravimetric analysis, field emission scanning electron microscopy, energy-dispersive X-ray analysis, X-ray diffraction, transmission electron microscopy, elemental analysis, inductively coupled plasma analysis and vibrating sample magnetometry. This catalytic system was found to be a highly active catalyst in the Mizoroki–Heck and Suzuki–Miyaura cross-coupling reactions. These reactions were best performed in dimethylformamide and water, respectively, in the presence of only 0.054 mol% of palladium under mild conditions. Moreover, the catalyst could be recovered easily and reused at least ten times without any considerable loss of its catalytic activity. Copyright
- Hajipour, Abdol R.,Tadayoni, Nayereh S.,Khorsandi, Zahra
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p. 590 - 595
(2016/07/16)
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