114772-53-1Relevant articles and documents
Microwave-assisted Negishi and Kumada cross-coupling reactions of aryl chlorides
Walla, Peter,Kappe, C. Oliver
, p. 564 - 565 (2004)
Rapid Pd or Ni-catalyzed microwave-accelerated Negishi and Kumada cross-coupling reactions of aryl chlorides in solution and on solid phase are reported.
4′-Methylbiphenyl-2-carbonitrile synthesis by continuous flow Suzuki-Miyaura reaction
Estrada, Gizelda O.D.,Flores, Marcella C.,Da Silva, Joaquim F.M.,De Souza, Rodrigo O.M.A.,E Miranda, Leandro S.M.
, p. 4166 - 4168 (2012)
In the present work we report a high selective synthesis of the bicyclic core present in an important angiotensin II inhibitor family of drugs (Sartans) under continuous flow conditions. The key step in our approach was a Suzuki-Miyaura coupling using for the first time the recently described 4-toluylboronic acid MIDA ester.
Maghemite decorated with ultra-small palladium nanoparticles (γ-Fe2O3-Pd): Applications in the Heck-Mizoroki olefination, Suzuki reaction and allylic oxidation of alkenes
Rathi, Anuj K.,Gawande, Manoj B.,Pechousek, Jiri,Tucek, Jiri,Aparicio, Claudia,Petr, Martin,Tomanec, Ondrej,Krikavova, Radka,Travnicek, Zdenek,Varma, Rajender S.,Zboril, Radek
, p. 2363 - 2373 (2016)
A nanocatalyst comprising ultra-small Pd/PdO nanoparticles (57Fe M?ssbauer spectroscopy. The cost-effective catalyst could be easily separated from the reaction mixture by using an external magnet and reused four times without any loss of activity; chemical stability and recyclability aspects of the catalyst were investigated.
Highly efficient palladium catalysts supported on nitrogen contained polymers for Suzuki-Miyaura reaction
Geng, Longfei,Li, Yan,Qi, Zhengliang,Fan, Haipeng,Zhou, Zhicheng,Chen, Rizhi,Wang, Yong,Huang, Jun
, p. 24 - 28 (2016)
Through Pd catalyzed C-N coupling reaction, Pd nanoparticles and diadamantylphosphine ligand were immobilized in situ into the formed N contained polymers as heterogeneous Pd catalysts for Suzuki-Miyaura reaction. The Pd@NPad2-1.0 catalyst was found to be highly efficient and only 4 ppm of Pd (Pd@NPad2-1.0) was required for the coupling of aryl bromides with phenylboronic acid, and the corresponding products were obtained in good to excellent yields with high TON and TOF as 250,000 and 41,666 h- 1 respectively. Moreover, the coupling of various aryl chlorides with phenylboronic acids gave the corresponding products in high yields also. And the Pd@NPad2-1.0 catalyst is reusable at least 5 times with only slight deactivation.
Benzyloxycalix[8]arene: A new valuable support for NHC palladium complexes in C-C Suzuki-Miyaura couplings
Abdellah, Ibrahim,Kasongo, Pauline,Labattut, Axel,Guillot, Régis,Schulz, Emmanuelle,Martini, Cyril,Huc, Vincent
, p. 13843 - 13848 (2018)
Benzyloxycalix[8]arene supported catalysts bearing N-heterocyclic carbene palladium complexes on each subunit were readily synthesized. Intermediates and catalysts were fully characterized, allowing for a fine control of their structure. X-ray diffraction analysis confirmed the formation of a calix[8]arene bearing eight well-defined NHC palladium complexes. The macrocyclic structure of calix[8]arenes allowed for a scalable and chromatography-free catalyst synthesis under homogeneous conditions, while the catalytic reaction proceeded under heterogeneous conditions, just by changing the nature of the solvent. Indeed, when used as a suspension in ethanol, a high TON and TOF were obtained through a large panel of functionalized brominated substrates in C-C Suzuki-Miyaura couplings, with low metal contamination after simple filtration.
Ligand-Promoted Direct C-H Arylation of Simple Arenes: Evidence for a Cooperative Bimetallic Mechanism
Kim, Jaewoon,Hong, Soon Hyeok
, p. 3336 - 3343 (2017)
A highly efficient catalyst for the direct C-H arylation of simple arenes was developed on the basis of a palladium-diimine complex. The developed catalyst exhibited the highest turnover number reported to date for the direct arylation of benzene due to increased stability provided by the diimine ligand. The reaction was also performed using only 2-3 equiv of simple arenes. Mechanistic studies in combination with kinetic measurements, isotope effect experiments, synthesis of possible intermediates, and stoichiometric reactions suggested that this reaction follows a cooperative bimetallic mechanism.
Palladium-catalyzed desulfitative cross-coupling of sodium arylsulfinates with aryl bromides and chlorides: An alternative convenient synthesis of biaryls
Zhou, Chao,Li, Yaming,Lu, Yang,Zhang, Rong,Jin, Kun,Fu, Xinmei,Duan, Chunying
, p. 1269 - 1273 (2013)
An alternative method for synthesis of biaryls has been developed through the Pd catalyzed desulfitative coupling reaction of sodium arylsulfinates with aryl bromides and chlorides. The procedure tolerates a variety of functional groups, such as cyano, formyl, acetyl, chloro, methoxy, trifluoromethyl and heteroaromatic unit. The desired products were obtained in moderate to excellent yields under relatively mild reaction conditions without additives, base or co-catalyst. An alternative method for synthesis of biaryls has been developed through the Pd catalyzed desulfitative coupling reaction of sodium arylsulfinates with aryl bromides and chlorides. The procedure tolerates a variety of functional groups, such as cyano, formyl, acetyl, chloro, methoxy, trifluoromethyl and heteroaromatic unit. The desired products were obtained in moderate to excellent yields under relatively mild reaction conditions without additives, base or co-catalyst. Copyright
Development of unimolecular tetrakis(piperidin-4-ol) as a ligand for Suzuki-Miyaura cross-coupling reactions: Synthesis of incrustoporin and preclamol
Nallasivam, Jothi L.,Fernandes, Rodney A.
, p. 3558 - 3567 (2015)
Abstract A domino aza-Cope/aza-Prins cascade enabled the synthesis of a new class of 4-hydroxypiperidine-appended mono, bis, tris, and tetrakis unimolecular compounds that served as efficient ligands to catalyze Suzuki-Miyaura cross-coupling reactions under aerobic conditions. Various biaryls, terphenyls, and heterocyclic biphenyls were obtained in good to excellent yields. The ligands were also capable of catalyzing the Heck-Mizoroki reaction. As an application, the Suzuki-Miyaura coupling reaction was used in the synthesis of incrustoporin, its analogs, and the drug molecule preclamol. A domino aza-Cope/aza-Prins cascade enabled the synthesis of a new class of 4-hydroxypiperidine-appended mono-, bis-, tris-, and tetrakis-unimolecular compounds that served as efficient ligands to catalyze Suzuki-Miyaura cross-coupling reactions under aerobic conditions. Various biaryls, terphenyls, and heterocyclic biphenyls were obtained in good to excellent yields.
A cross-coupling synthesis of functionalised biaryls using Knochel-type organozinc reagents and a pyridine enhanced palladium catalyst
Wang, Min,Liu, Fang,Zeng, Meng-Tian,Xu, Wan,Liu, Min,Dong, Zhi-Bing
, p. 382 - 384 (2016)
A variety of functionalised biaryls were synthesised on the 20-30 mmol scale by using Knochel type organozinc reagents (organozinc reagents prepared from aryl halides, Zn powder and LiCl) catalysed by PEPPSI (a pyridine enhanced palladium catalyst). The protocol enabled the Negishi reactions to proceed in a smooth, rapid and mild way to give the corresponding products in excellent yields (80 ～ 96%). Sensitive functional groups, such as CN and COOEt groups, were tolerated in the coupling reaction.
Cu-Catalyzed Denitrogenative Ring-Opening of 3-Aminoindazoles for the Synthesis of Aromatic Nitrile-Containing (Hetero)Arenes
Zhou, Yao,Deng, Shuilin,Mai, Shaoyu,Song, Qiuling
, p. 6161 - 6165 (2018)
An unprecedented Cu-catalyzed oxidative cleavage of two C-N bonds of 3-aminoindazoles is reported herein, which represents the first example for denitrogenative ring-opening of 3-aminoindazoles. This novel reactivity of 3-aminoindazoles enables the produc
Investigations into the Suzuki-Miyaura coupling aiming at multikilogram synthesis of E2040 using (o-cyanophenyl)boronic esters
Urawa, Yoshio,Naka, Hiroyuki,Miyazawa, Mamoru,Souda, Shigeru,Ogura, Katsuyuki
, p. 269 - 278 (2002)
The Suzuki-Miyaura cross-coupling reaction between 1-{3-bromo-4-chloro-5-[1-(R)-fluoropropyl]}phenylpiperazine ((R)-1b) and thermally unstable (0-cyanophenyl)boronic ester 6b in the presence of dichlorobis(triphenylphosphine)palladium and potassium phosph
Synthetic applications of oxime-derived palladacycles as versatile catalysts in cross-coupling reactions
Alonso, Diego A.,Botella, Luis,Najera,Pacheco, Ma. Carmen
, p. 1713 - 1718 (2004)
Palladacycles 1 and 2, derived from 4,4′-dichlorobenzophenone and 4-hydroxyacetophenone oximes, respectively, are very efficient and versatile pre-catalysts for a wide range of carbon-carbon bond coupling reactions such as, Mizoroki-Heck, Suzuki-Miyaura, Stille, Ullmann-type, Sonogashira, sila-Sonogashira, Glaser and acylation of alkynes under very low loading conditions in air and either in organic or aqueous solvents, employing reagent-grade chemicals. High yielding, general, and practical procedures for the palladium-catalyzed Mizoroki-Heck, Suzuki-Miyaura, Ullmann-type, Sonogashira and sila-Sonogashira reactions are described.
Palladium Supported on Graphitic Carbon Nitride: An Efficient and Recyclable Heterogeneous Catalyst for Reduction of Nitroarenes and Suzuki Coupling Reaction
Zhao, Yukai,Tang, Ruiren,Huang, Rong
, p. 1961 - 1971 (2015)
In this study, a novel platelet-like nanocatalyst, Pd/g-C3N4 with easily approachable active sites, was developed. The mesoporous graphitic carbon nitride (g-C3N4) is a layered structure connected by planar amino groups, which can work as stabilizer and active support for noble metal nanoparticles. The palladium nanoparticles with an average particle size of 3.25 nm were evenly dispersed on the surface of g-C3N4 without aggregation. Detailed charaterizations reveal that there is no covalent-bond interaction between g-C3N4 and Pd NPs. The Pd/g-C3N4 catalyst showed excellent catalytic activity in the reduction of nitroarenes by NaBH4, and Suzuki coupling reaction of aryl halides with arylboronic acids under mild conditions. The reduction of 4-nitrophenol has a pseudo-first-order rate constant of 7.29 × 10-3 s-1, and an activity parameter of 1.37 s-1 mM-1, which is higher than those reported in the literature. Furthermore, the Suzuki coupling reactions processed smoothly with 97.0 % isolate yield in less than 30 min in water with PEG600 as the additive. The catalyst could be recycled for five times without significant loss of catalytic activity, which confirmed the good stability of the catalyst. Graphical Abstract: [Figure not available: see fulltext.]
Cathodic aromatic C,C cross-coupling reaction via single electron transfer pathway
Qu, Yang,Tateno, Hiroyuki,Matsumura, Yoshimasa,Kashiwagi, Tsuneo,Atobe, Mahito
, (2017)
We have successfully developed a novel cathodic cross-coupling reaction of aryl halides with arenes. Utilization of the cathodic single electron transfer (SET) mechanism for activation of aryl halides enables the cross-coupling reaction to proceed without the need for any transition metal catalysts or single electron donors in a mild condition. The SET from a cathode to an aryl halide initiates a radical chain by giving an anion radical of the aryl halide. The following propagation cycle also consists entirely of anion radical intermediates.
Trinuclear copper(I) complex of 1,3-bis(2-pyridinylmethyl)imidazolylidene as a carbene-transfer reagent for the preparation of catalytically active nickel(II) and palladium(II) complexes
Chen, Chao,Qiu, Huayu,Chen, Wanzhi
, p. 4166 - 4172 (2012)
Reactions of 1,3-bis(pyridin-2-ylmethyl)-1H-imidazol-3-ium hexafluorophosphate, ([HL1](PF6), L1 = 1,3-bis(pyridin-2-ylmethyl) imidazolylidene) and 1,3-bis(pyridin-2-ylmethyl)-1H-benzimidazol-3-ium hexafluorophosphate ([HL2](PF6), L2 = 1,3-bis(pyridin-2-ylmethyl) benzoimidazolylidene) with cuprous oxide in acetonitrile readily yielded trinuclear complexes [Cu3(L1)3(PF6) 3] (1) and [Cu3(L2)3(PF6) 3] (2). Treatment of 1 with Ni(PPh3)2Cl 2 and Pd(cod)Cl2 gave [Ni(L1)Cl](PF6) (3) and [Pd(L1)Cl](PF6) (4), respectively, due to transmetalation. [Ni(L1)2](PF6)2 (5) was obtained from the reaction of [Cu3(L1)3(PF6)3] and Raney nickel in acetonitrile. All these complexes have been fully characterized. Both 1 and 2 consist of a triangular Cu3 core with each Cu-Cu bond capped by an imidazolylidene group. Each imidazolylidene acts as a bridging ligand in a μ2 mode and is bonded equally to two Cu(I) ions. The pincer nickel and palladium complexes are square-planar and contain a tridentate NCN ligand. Complexes 3 and 4 are efficient catalyst precursors for Kumada-Corriu and Suzuki-Miyaura coupling reactions of aryl halides with organometallic reagents.
Molecular sieves-supported palladium(II) catalyst: Suzuki coupling of?chloroarenes and an easy access to useful intermediates for the synthesis of?irbesartan, losartan and boscalid
Dey, Raju,Sreedhar, Bojja,Ranu, Brindaban C.
, p. 2301 - 2305 (2010)
Palladium(II) chloride supported on 4 ? molecular sieves efficiently catalyzes the Suzuki coupling reactions of chlorobenzenes in presence of tetrabutylammonium bromide without any ligand. The useful intermediates for the synthesis of bioactive compounds such as irbesartan, and losartan have been prepared in one step following this reaction. The preparation of this catalyst is very simple. The FE-SEM image shows a cube shape ordered structure. The catalyst does not exhibit any nanoparticles as indicated by TEM. EDS and XPS demonstrate anchoring of Pd on molecular sieves in +2 oxidation state. This heterogeneous catalyst is stable, non-air sensitive and recyclable.
Manganese-Catalyzed Cross-Coupling of Aryl Halides and Grignard Reagents by a Radical Mechanism
Antonacci, Giuseppe,Ahlburg, Andreas,Fristrup, Peter,Norrby, Per-Ola,Madsen, Robert
, p. 4758 - 4764 (2017)
The substrate scope and the mechanism have been investigated for the MnCl2-catalyzed cross-coupling reaction between aryl halides and Grignard reagents. The transformation proceeds rapidly and in good yield when the aryl halide component is an aryl chloride containing a cyano or an ester group in the para position or a cyano group in the ortho position. A range of other substituents gave no conversion of the aryl halide or led to the formation of side products. A broader scope was observed for the Grignard reagents, where a variety of alkyl- and arylmagnesium chlorides participated in the coupling. Two radical-clock experiments were carried out, and in both cases an intermediate aryl radical was successfully trapped. The cross-coupling reaction is therefore believed to proceed by an SRN1 mechanism, with a triorganomanganate complex serving as the most likely nucleophile and single-electron donor. Other mechanistic scenarios were excluded based on the substrate scope of the aryl halide.
New Practical Syntheses of 4′-Methylbiphenyl-2-carbonitrile and -2-carbaldehyde
Goubet, Dominique,Meric, Pascal,Dormoy, Jean-Robert,Moreau, Patrice
, p. 4516 - 4518 (1999)
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Cyanide-Free Cyanation of sp2 and sp-Carbon Atoms by an Oxazole-Based Masked CN Source Using Flow Microreactors
Sharma, Brijesh M.,Nikam, Arun V.,Lahore, Santosh,Ahn, Gwang-Noh,Kim, Dong-Pyo
supporting information, (2022/02/25)
This work reports a cyanide-free continuous-flow process for cyanation of sp2 and sp carbons to synthesize aryl, vinyl and acetylenic nitriles from (5-methyl-2-phenyloxazol-4-yl) boronic acid [OxBA] reagent as a sole source of carbon-bound mask
A recyclable self-supported nanoporous PdCu heterogeneous catalyst for aqueous Suzuki-Miyaura cross-coupling
Chen, Jie,Du, Jialei,Liu, Fushan,Wang, Bin,Wang, Leichen,Xia, Hehuan,Xiang, Daili,Xu, Caixia,Zhang, Yuanyuan,Zhao, Yiwei
supporting information, p. 11641 - 11644 (2021/11/12)
Nanoporous PdCu (NP-PdCu) was prepared by the dealloying strategy from a PdCuAl ternary alloy precursor and characterized systematically using SEM, TEM, XRD, and XPS. NP-PdCu was demonstrated to be a competent self-supported heterogenous catalyst for Suzuki-Miyaura cross-coupling, affording a series of synthetically valuable biaryl compounds in good to excellent yields. This catalyst could be easily separated from the productviacentrifugation and reused several times without obvious loss of catalytic performance.
Organozinc-mediated direct cross-coupling under microwave irradiation
Li, Chun-Jing
, p. 869 - 875 (2021/07/02)
We report a direct cross-coupling reaction between (het)aryl pivalates/tosylates and di(het)arylzinc species in 2-methyltetrahydrofuran/N-methyl pyrrolidone (1:1), which occurs via C–O bond cleavage under microwave irradiation. The reaction takes place smoothly in short reaction times without the addition of any catalyst or ligand. The reaction is suitable for a broad scope of substrates and exhibits good functional group compatibility, utilizes a simple work-up procedure, and gives the desired products in high purity.
