cas 2216-12-8, 2-NITRODIPHENYL ETHER | Articles data

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Henley
p. 1222
(1930)
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Heterogeneous O -arylation of nitroarenes with substituted phenols over a copper immobilized mesoporous silica catalyst
Highly porous and robust mesoporous silica, SBA-15 has been subjected to post-synthesis modification for the anchoring of copper through Schiff base moiety formation using the silicon alkoxide route. The hybrid porous material has been fully characterized by powder-XRD, electronic spectra, EPR, thermogravimetric analysis, N2 sorption measurements, and TEM and SEM/EDS studies. The efficiency of the catalyst has been assessed in the O-arylation reaction using various substituted phenols and nitroarenes in heterogeneous conditions. The catalytic coupling reaction efficiently produces unsymmetrical diaryl ethers. The impressive capability to activate substrates having electron-donating or electron-withdrawing substituents and to have a high turnover frequency in the catalytic reactions made the catalyst highly desirable.
Maity, Tanmoy,Bhunia, Susmita,Das, Soma,Koner, Subratanath
p. 33380 - 33386
(2016)
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Ligand-free copper-catalyzed O-arylation of arenesulfonamides with phenols: An unusual approach to biaryl ether synthesis
An unprecedented ligand-free copper-catalyzed O-arylation of arenesulfonamides with phenols has been developed. Thus, a range of unsysmmetric biaryl ethers were synthesized in excellent yields. The reaction occurs efficiently with excellent regioselectivity through the cleavage of Cary–S bond and with a good tolerance of functional groups on the phenyl ring of phenols. The reaction is appreciated for its readily accessible substrates, mild conditions, and simple operation under air.
Chen, Junmin,Wang, Junmin,Chen, Xida,Huang, Yuming,Shouzhi, Pu
p. 836 - 843
(2019)
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Thermally stable and robust gadolinium-based metal-organic framework: Synthesis, structure and heterogeneous catalytic O-arylation reaction
Hydrothermal treatment of gadolinium nitrate and 2,6-naphthalenedicarboxylic acid (H2NDC) afforded a new metal-organic framework compound, {[Gd4(NDC)6(H2O)6]·2H2O}n(1). Compound 1 has been characterized by single-crystal X-ray crystallography, elemental analysis, FT-IR spectroscopy, therrmogravimetric analysis (TGA) and powder X-ray diffraction analysis. It is crystallized in the monoclinic system with the P21/n space group. Four crystallographically distinct Gd (III) centres are interconnected with each other through bridged carboxylato oxygen atoms and water molecules to form tetranuclear secondary building units, which are further connected through the carboxylato ligand and the network propagates along the crystallographic ac plane to form a 2D structure. Subsequent reinforcement from the remaining carboxylato oxygen atoms gives rise to a robust 3D framework structure. Thermogravimetric analysis demonstrates that compound 1 is fairly stable after dehydration under a nitrogen atmosphere. Notably, compound 1 is capable of catalyzing the O-arylation reaction efficiently between substituted phenols and bromoarene under heterogeneous conditions at 80 °C to afford unsymmetrical diarylethers.
Ghosh, Pameli,Maity, Tanmoy,Biswas, Saptarshi,Debnath, Rakesh,Koner, Subratanath
(2020/12/21)

Solvent-free palladium-catalyzed C–O cross-coupling of aryl bromides with phenols
A new solvent-free procedure for C–O cross-coupling between phenols and aryl bromides comprising of Pd2(dba)3/ButBrettPhos catalytic system is efficient for substrates bearing donor or acceptor, as well as bulky substituents.
Asachenko, Andrey F.,Bogachev, Vasilii N.,Cherkashchenko, Ilia R.,Lavrov, Konstantin V.,Minaeva, Lidiya I.,Nechaev, Mikhail S.,Rzhevskiy, Sergey A.,Sterligov, Grigorii K.,Topchiy, Maxim A.
p. 409 - 411
(2021/06/07)

Preparation method of secondary aromatic amine
The invention provides a method for preparing secondary aromatic amine by performing a palladium-catalyzed C-N coupling reaction on (pseudo)aryl halide and (pseudo)heterocyclic aryl halide and primary(heterocyclic)aromatic amine. The method is characterized in that an alkali for promoting the reaction is an alkali metal carboxylate or an alkali metal bicarbonate.
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(2021/03/31)

Preparation and characterization of Cu based on 5,5'-bistetrazole as a recyclable metal-organic framework and application in synthesis of diaryl ether by the Ullmann coupling reaction
Cu based on 5,5′-bistetrazole ([Cu2BT · 2H2O] n) as a recyclable metal-organic framework (MOF) heterogeneous catalyst was characterized by FT-IR, 13C NMR, XRD, SEM, EDX, BET, BJH, and ICP-AES analysis. The catalytic activity of the catalyst was probed through the Ullmann reaction for synthesis of diaryl ether derivatives from two component reactions of aromatic arylhalides and phenol derivatives in DMSO. Simple procedure, high yields, short reaction time, and environmentally benign methods are advantages of this protocol. The catalyst was readily separated by simple filtration and reusable without significant loss of its catalytic efficiency.
Noorpoor, Zeinab,Tavangar, Saeed
p. 1651 - 1662
(2021/05/10)

A novel magnetic polyacrylonotrile-based palladium Core?Shell complex: A highly efficientcatalyst for Synthesis of Diaryl ethers
The present article describes the synthesis of a new magnetic polyacrylonitrile-based Pd catalyst involving polyacrylonitrile modified via 2-aminopyridine as an efficient support to immobilize Pd nanoparticles. The simple reusability, easy separation and high stability of this Pd complex make it an excellent candidate to generate a C–O bond via Ph-X activation which is a really important subject in achieving biologically active compounds. It is worth to note access to good and high yields as well as broad substrate scope have resulted from superior reactivity of this catalyst complex. Furthermore, the structure of the magnetic polyacrylonitrile-based heterogeneous catalyst was characterized by fourier transmission infrared (FT-IR) spectroscopy, field emission scanning electron microscopy (FE-SEM) and transmission electron microscopy (TEM), X-ray diffraction (XRD). Also, its thermal properties were studied by thermogravimetric analysis (TGA).
Eslami, Mohammad,Jarahiyan, Atefeh,Moghaddam, Firouz Matloubi,Pourjavadi, Ali
(2020/04/15)

Exploration of Fragment Binding Poses Leading to Efficient Discovery of Highly Potent and Orally Effective Inhibitors of FABP4 for Anti-inflammation
Fatty-acid binding protein 4 (FABP4) is a promising therapeutic target for immunometabolic diseases, while its potential for systemic inflammatory response syndrome treatment has not been explored. Here, a series of 2-(phenylamino)benzoic acids as novel and potent FABP4 inhibitors are rationally designed based on an interesting fragment that adopts multiple binding poses within FABP4. A fusion of these binding poses leads to the design of compound 3 with an ?460-fold improvement in binding affinity compared to the initial fragment. A subsequent structure-aided optimization upon 3 results in a promising lead (17) with the highest binding affinity among all the inhibitors, exerting a significant anti-inflammatory effect in cells and effectively attenuating a systemic inflammatory damage in mice. Our work therefore presents a good example of lead compound discovery derived from the multiple binding poses of a fragment and provides a candidate for development of drugs against inflammation-related diseases.
Su, Haixia,Zou, Yi,Chen, Guofeng,Dou, Huixia,Xie, Hang,Yuan, Xiaojing,Zhang, Xianglei,Zhang, Naixia,Li, Minjun,Xu, Yechun
p. 4090 - 4106
(2020/05/20)

Copper(I)–creatine complex on magnetic nanoparticles as a green catalyst for N- and O-arylation in deep eutectic solvent
Immobilization of copper(I) ions on magnetic nanoparticles was performed using surface modification of Fe3O4 with creatine. Fe3O4?creatine-Cu(I) magnetic catalyst was synthesized and applied in C&bond;X cross-coupling reactions with aryl halides in a deep eutectic as a green solvent. The results indicate the Fe3O4?creatine-Cu(I) magnetic nanoparticles showed excellent activity and high stability. In addition, it was revealed that this catalyst can be recycled five times without significant loss in catalytic activity.
Bagheri, Sepideh,Heydari, Akbar,Pazoki, Farzane,Radfar, Iman
(2020/01/22)

Pd based on 2-Aminopyrimidine and 1H-benzo[d]imidazol-2-amine functionalizedFe3O4 nanoparticles as novel recyclable magnetic nanocatalysts for Ullmann coupling reaction
In this study, Pd based on 2-Aminopyrimidine and 1H-benzo[d]imidazol-2-amine functionalized Fe3O4 magnetic nanoparticles [(Pd-APM-PSi-Fe3O4) and (Pd-BIA-PSi-Fe3O4)] was designed and used for the synthesis of di aryl ether by Ulmann cross-coupling reactions. Ulmann reaction performed with mixing of the arylhalides and phenol derivatives in DMF solvent. The prepared catalysts were characterized with various analytical techniques such as FT-IR, XRD, TGA, SEM, TEM, EDX, ICP and VSM. Pd-APM-PSi-Fe3O4 and Pd-BIA-PSi-Fe3O4 catalysts demonstrated good to excellent yields catalytic efficiency for Ulmann reactions in comparison with to commercial palladium catalysts. The catalyst is easily recycled and reused without loss of the catalytic activity. The combined merits of reusable catalyst conditions make the condensation with safe operation, no leaching of pd into environment, low pollution, rapid access to products and simple workup. Also, these novel magnetic nanocatalysts are superior to the industry standard Pd in every relevant aspect. They feature a way higher initial activity, a much more convenient separation, better recycling, and less contamination of the products. Last but not least, they can be very easily prepared from commercially available Fe3O4 nanoparticles using standard laboratory equipment.
Chen, Jin,Dai, Linfang,Li, Jiayu,Mohammadnia, Majid
(2020/05/25)

CoII Immobilized on Aminated Magnetic-Based Metal–Organic Framework: An Efficient Heterogeneous Nanostructured Catalyst for the C–O Cross-Coupling Reaction in Solvent-Free Conditions
Abstract: In this paper, we report the synthesis of Fe3O4?AMCA-MIL53(Al)-NH2-CoII NPs based on the metal–organic framework structures as a magnetically separable and environmentally friendly heterogeneous nanocatalyst. The prepared nanostructured catalyst efficiently promotes the C–O cross-coupling reaction in solvent-free conditions without the need for using toxic solvents and/or expensive palladium catalyst. Graphic Abstract: [Figure not available: see fulltext.].
Mohammadinezhad, Arezou,Akhlaghinia, Batool
p. 332 - 352
(2020/01/11)

A 3 - benzofuran bromine two synthetic method (by machine translation)
The invention relates to a 3 - benzofuran bromine two synthetic method, which belongs to the field of organic synthesis, the method uses 2 - fluoro nitrobenzene and phenol as the starting material, through the nucleophilic substitution reaction synthesis of 2 - nitro-diphenyl ether, reduction to obtain 2 - amino-diphenyl ether, brominated to obtain 2 - amino - 5 - bromine two ether, diazotization to obtain the corresponding four fluoro boric acid diazonium salt, ferrous sulfate obtained by catalytic ring 3 - bromine two benzofuran. The route of low raw material cost, high product yield, simple process operation, while avoiding the use of the noble metal catalyst, in the industrial production has significant economic advantage and environmental protection. (by machine translation)
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(2019/07/10)

Cell-Based Optimization of Covalent Reversible Ketoamide Inhibitors Bridging the Unprimed to the Primed Site of the Proteasome β5 Subunit
The ubiquitin-proteasome system (UPS) is an established therapeutic target for approved drugs to treat selected hematologic malignancies. While drug discovery targeting the UPS focuses on irreversibly binding epoxyketones and slowly-reversibly binding boronates, optimization of novel covalent-reversibly binding warheads remains largely unattended. We previously reported α-ketoamides to be a promising reversible lead motif, yet the cytotoxic activity required further optimization. This work focuses on the lead optimization of phenoxy-substituted α-ketoamides combining the structure-activity relationships from the primed and the non-primed site of the proteasome β5 subunit. Our optimization strategy is accompanied by molecular modeling, suggesting occupation of P1′ by a 3-phenoxy group to increase β5 inhibition and cytotoxic activity in leukemia cell lines. Key compounds were further profiled for time-dependent inhibition of cellular substrate conversion. Furthermore, the α-ketoamide lead structure 27 does not affect escape response behavior in Danio rerio embryos, in contrast to bortezomib, which suggests increased target specificity.
Stubba, Daniel,Bensinger, Dennis,Steinbacher, Janika,Proskurjakov, Lilia,Salcedo Gómez, álvaro,Schmidt, Uwe,Roth, Stefan,Schmitz, Katja,Schmidt, Boris
supporting information
p. 2005 - 2022
(2019/11/22)

COMPOUND AND ORGANIC ELECTRONIC DEVICE USING THE SAME
Provided are a novel compound and an organic electronic device using the same. The novel compound is represented by the following Formula (I): wherein Y is an oxygen atom or a sulfur atom; X1 and X2 are each independently C(Ra), the two (Ra)s are the same or different, and the two (Ra)s are joined together to form a first aryl ring; X3 and X4 are each independently C(Rb), the two (Rb)s are the same or different, and the two (Rb)s are joined to form a second aryl ring or a heteroaryl ring.
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(2019/04/14)

Ligand-free Cu(ii)-catalyzed aerobic etherification of aryl halides with silanes: An experimental and theoretical approach
Owing to their wide occurrence in nature and immense applications in various fields, the synthesis of aryl alkyl ethers has remained a focus of interest. In contrast to the conventional/traditional methods of etherification, herein, we have reported a more efficient method, which is better yielding and more general in application. The etherification of aryl halides by alkoxy/phenoxy silanes was catalyzed by copper acetate in the presence of cesium carbonate and oxygen in DMF at 145 °C. All the as-synthesized compounds were characterized via the 1H-NMR and 13C-NMR spectroscopic techniques. Density functional theory calculations using the B3LYP functional were performed to elucidate the reaction mechanism. The C-O coupling reaction between 2-nitroiodobenzene and tetramethoxysilane was used as a model reaction. The activation energy barriers for the generation of catalytic species (31.6 kcal mol-1) and the σ-bond metathesis (16.0 kcal mol-1), oxidative addition/reductive elimination (20.3 kcal mol-1), halogen atom transfer (19.2 kcal mol-1) and single electron transfer (SET) (29.5 kcal mol-1) mechanisms for the C-O coupling reaction were calculated. Calculations for the key reaction steps were repeated with the B3PW91, PBEH1PBE, wB97XD, CAM-B3LYP and mPW1LYP functionals. The formation of catalytic species via a single electron transfer reaction between tetramethoxysilane and copper acetate, formation of methoxy radicals and methoxylation of copper showed an overall energy barrier of 31.6 kcal mol-1, and therefore is the rate determining step.
Ahmed, Muhammad Naeem,Ahmad, Khalil,Yasin, Khawaja Ansar,Farooq, Tayyaba,Khan, Bilal Ahmad,Roy, Soumendra K.
p. 11316 - 11333
(2019/07/31)

Fe3O4@SiO2-copper sucrose xanthate as a green nanocatalyst for N-, O- and S-arylation
Formation of C(sp2)–X bonds was carried out using a Fe3O4@SiO2-copper(I) sucrose xanthate nanoparticle catalyst with the aid of the copper(I) xanthate moiety in the catalyst which was prepared from the reaction between sucrose and carbon disulfide through an alkaline medium via the traditional Zeise approach. Various techniques were employed for the characterization of these novel nanoparticles. Three sorts of heteroatoms, N, O and S, successfully underwent heteroatom arylation to produce secondary or tertiary amines, ethers and thioethers, respectively.
Radfar, Iman,Kazemi Miraki, Maryam,Esfandiary, Naghmeh,Ghandi, Leila,Heydari, Akbar
(2019/01/04)

Preparation and characterization of isatin complexed with Cu supported on 4-(aminomethyl) benzoic acid-functionalized Fe3O4 nanoparticles as a novel magnetic catalyst for the Ullmann coupling reaction
Isatin complexed with Cu supported on 4-(aminomethyl) benzoic acid-functionalized Fe3O4 nanoparticles (Cu-IS-AMBA-MNPs) as a new catalyst was designed, prepared and characterized by appropriate analyses. The heterogeneous reusable catalyst was successfully used for the efficient and widespread syntheses of diaryl ethers and diarylamines via the Ullmann coupling reaction. This green catalyst was easily removed, reused several times with no significant loss of its activity, and provided a clean synthesis with excellent yield and reduced time.
Khodaei, Mohammad Mehdi,Alizadeh, Abdolhamid,Haghipour, Maryam
p. 2727 - 2747
(2019/02/13)

COMPOUND AND ORGANIC ELECTRONIC DEVICE USING THE SAME
Provided are a novel compound and an organic electronic device using the same. The novel corn pound is represented by the following Formula (I): wherein Y is an oxygen atom, a sulfur atom, or a sulfur dioxide group; X1 and X2 are each independently C(Ra), multiple (Ra)s are the same or different, and the two (Ra)s are joined together to form a first aryl ring; X3 and X4 are each independently C(Rb), multiple (Rb)s are the same or different, and the two (Rb)s are joined to form a second aryl ring or a heteroaryl ring.
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(2018/06/15)

COMPOUND AND ORGANIC ELECTRONIC DEVICE USING THE SAME
Provided are a novel compound and an organic electronic device using the same. The novel compound is represented by the following Formula (I): wherein Y is an oxygen atom or a sulfur atom; X 1and X 2are each independently C(R a), the two(R a)s are the same or different, and the two (R a)s are joined together to form a first aryl ring; X 3and X 4are each independently C(R b), the two (R b)s are the same or different, and the two (R b)s are joined to form a second aryl ring or a heteroaryl ring.
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(2019/04/30)

8-exo-dig-Selective Cycloisomerization for the Synthesis of Dibenzo[b,e][1,4]diazocines Using Cationic AuI Catalysts
The cationic AuI-catalyzed intramolecular reaction of N-propargyl-2-anilinoanilines gave a diazocine skeleton via 8-exo-dig-selective cycloisomerization by the suppression of 6-endo-dig cycloisomerization. Both terminal and internal alkynes could be used according to the choice of ligand of the AuI complex, and various dibenzo[b,e][1,4]diazocines were obtained. Control experiments suggested that two nitrogen atoms in the tether of substrates were critical in this selective transformation.
Ito, Mamoru,Inoue, Daisuke,Takaki, Asahi,Kanyiva, Kyalo Stephen,Shibata, Takanori
supporting information
p. 4740 - 4747
(2018/09/14)

Immobilized palladium nanoparticles on MNPs@A-N-AEB as an efficient catalyst for C-O bond formation in water as a green Solvent
Palladium nanoparticles immobilized on the magnetic nanoparticles@2-amino-N-(2-aminoethyl) benzamide (MNPs@A-N-AEB.Pd0) have been presented as an efficient, and reusable magnetically heterogeneous catalyst for the C-O coupling reaction, namely Ullmann condensation reactions in an aqueous medium. This heterogeneous catalyst shows superior reactivity for the C-O arylation of different aryl halide (chloride, bromide, and iodide) with phenol derivatives to afford the desired products in good to excellent yields within short reaction time. Moreover, the catalyst can be easily recovered and reused for seven runs without loss of catalytic activity. The catalyst was characterized by several techniques, such as FT-IR, SEM, TEM, EDS, XRD, TGA and ICP-OES.
Moghaddam, Firouz Matloubi,Eslami, Mohammad
(2018/08/24)

Synthesis of medium-sized (6-7-6) ring compounds by iron-catalyzed dehydrogenative C-H activation/annulation
In this report, we have described a FeCl3-catalyzed process involving intramolecular annulation of o-phenoxy diarylacetylenes via hydroarylation to afford a series of biologically potent fused seven-membered (6-7-6) ring compounds under mild reaction conditions. This reaction was believed to proceed through Friedel-Crafts type sequential carbometallation followed by protonation to produce phenyldibenz[b,f]oxepines. This method was also extended to synthesize seven-membered rings that are fused with coumarins.
Panda, Niranjan,Mattan, Irshad,Ojha, Subhadra,Purohit, Chandra Shekhar
supporting information
p. 7861 - 7870
(2018/11/21)

Copper immobilized on magnetite nanoparticles coated with ascorbic acid: An efficient and reusable catalyst for C─N and C─O cross-coupling reactions
In a continuation of using magnetic nanoparticle (MNP)-supported catalysts, ascorbic acid (readily available, very safe and with strong affinity to MNPs) was used instead of the commonly used silica layer coating. This hybrid was used for immobilizing copper nanoparticles to produce Cu/ascorbic acid@MNPs catalyst. The catalyst was characterized and used in carbon–oxygen and carbon–nitrogen (various substrates) cross-coupling reactions in aqueous media and at room temperature with excellent product yields. Furthermore, the catalyst could be quickly and completely recovered using an external magnetic field and reused for six reaction cycles without significant change in catalytic activity.
Hajipour, Abdol R.,Check, Maryam,Khorsandi, Zahra
(2017/09/30)

Cellulose-supported N-heterocyclic carbene silver complex with pendant ferrocenyl group for diaryl ether synthesis
A cellulose-supported N-heterocyclic carbene Ag(I) complex has been synthesized by covalent grafting of ferrocenyl ionic liquid in the matrix of cellulose followed by metallation with silver oxide. The complex was employed as a heterogeneous catalyst in the synthesis of diaryl ethers. Reactions of a variety of phenols with aryl halides afford corresponding diaryl ethers in moderate to good yields. Recyclability experiments were executed successfully for five consecutive runs.
Jagadale, Megha,Salunkhe, Rajashri,Kumbhar, Arjun,Gajare, Shivanand,Rajmane, Mohan,Rashinkar, Gajanan
(2017/03/01)

The Suzuki-Miyaura Coupling of Nitroarenes
Synthesis of biaryls via the Suzuki-Miyaura coupling (SMC) reaction using nitroarenes as an electrophilic coupling partners is described. Mechanistic studies have revealed that the catalytic cycle of this reaction is initiated by the cleavage of the aryl-nitro (Ar-NO2) bond by palladium, which represents an unprecedented elemental reaction.
Yadav, M. Ramu,Nagaoka, Masahiro,Kashihara, Myuto,Zhong, Rong-Lin,Miyazaki, Takanori,Sakaki, Shigeyoshi,Nakao, Yoshiaki
supporting information
p. 9423 - 9426
(2017/07/24)

Access to Chiral Seven-Member Cyclic Amines via Rh-Catalyzed Asymmetric Hydrogenation
A highly efficient asymmetric hydrogenation of azepine/oxazepine-type seven-member cyclic imine hydrochlorides was successfully developed using Rh/bisphosphine-thiourea ligand ZhaoPhos, affording various chiral seven-member cyclic amines with full conversions, high yields, and excellent enantioselectivities (up to 96% yield, >99% ee). Additionally, this asymmetric hydrogenation can proceed well on gram scale with excellent ee value. Moreover, control experimental results displayed that the anion-bonding interaction between the chloride ion of the substrate and thiourea motif of the ZhaoPhos played an important role to obtain excellent enantioselectivity.
Li, Pan,Huang, Yi,Hu, Xinquan,Dong, Xiu-Qin,Zhang, Xumu
supporting information
p. 3855 - 3858
(2017/07/26)

Ullmann Coupling Reaction of Nitro-Substituted Aryl Halides with Phenols under Mild Conditions: Micro-/Mesoporous Hierarchical LaAlPO-5 Zeolite Catalyst
Heterogeneous catalytic reactions of aromatic organic molecules over zeolite catalysts present many challenges because of the shape selectivity of the micropores of conventional zeolites that limits the diffusion of aromatic molecules. Herein, Ullmann coupling reactions of phenols with nitro-substituted aryl halides were catalyzed by rare-earth-doped mesoporous AlPO-5 zeolites in the absence of ligands. The AlPO-5-MAlPO-5-M zeolites had a pure AFI structure and consisted of spherical particles assembled by nanofibers. The rare-earth elements were highly dispersed in the AlPO-5-MAlPO-5-M samples. The LaAlPO-5-MAlPO-5-M zeolite is an excellent catalyst for Ullmann coupling reactions of phenols and nitro-substituted aryl halides. Mesoporous LaAlPO-5 has an excellent stability and recyclability in the Ullmann coupling of p-X-nitrobenzene (X=Cl, Br, and I) with 2-naphthol. These results are important in the exploration of attractive Ullmann coupling reactions and in the development of mesoporous zeolite catalysts for other organic reactions.
Ke, Qingping,Wu, Mingzhou,Wang, Chao,Lu, Guanzhong
p. 1557 - 1563
(2016/05/02)

Facile aromatic nucleophilic substitution (SNAr) reactions in ionic liquids: An electrophile-nucleophile dual activation by [Omim]Br for the reaction
A facile aromatic nucleophilic substitution (SNAr) reaction in recyclable [Omim]Br under relatively mild conditions has been described. An electrophile-nucleophile dual activation by [Omim]Br is also discovered based on control experiments, 1H NMR and IR spectroscopies. This chemistry provides an efficient and metal-free approach for the generation of Caryl-X (XS, N, O) bonds, many of which are significant synthetic intermediates or drugs, making this methodology attractive to both synthetic and medicinal chemistry.
Zhang, Xiao,Lu, Guo-Ping,Cai, Chun
p. 5580 - 5585
(2016/10/21)

Design, synthesis and antifungal activity of novel furancarboxamide derivatives
Twenty-seven novel furancarboxamide derivatives with a diphenyl ether moiety were synthesized and evaluated for their antifungal activity against Rhizoctonia solani, Botrytis cirerea, Valsa Mali and Sphaceloma ampelimum. Antifungal bioassay results indicated that most compounds had good or excellent fungicidal activities for R. solani and S. ampelimum at 20 mg L-1. Among synthesized compounds, compound 18e showed a greater inhibitory effect against S. ampelimum, with half maximal effective concentration (EC50) values of 0.020 mg L-1. This strong activity rivals currently used commercial fungicides, such as Boscalid and Carbendazim, and has great potential as a lead compound for future development of novel fungicides.
Wen, Fang,Jin, Hong,Tao, Ke,Hou, Taiping
p. 244 - 251
(2016/05/24)

Visible-light-mediated synthesis of diaryl ethers from arylboronic acids and diaryliodonium salts
With visible-light irradiation, a simple and metal-free photocatalytic system for the synthesis of diaryl ethers from arylboronic acids and diaryliodonium salts has been developed. The reaction proceeded in high yield for a range of different substrates in the presence of eosin Y under mild reaction conditions.
Liu, Li,Tang, Jiaqi,Qiang, Jian,Li, Jian,He, Mingyang
p. 261 - 264
(2016/07/06)

Interface Engineering in Two-Dimensional Heterostructures: Towards an Advanced Catalyst for Ullmann Couplings
The design of advanced catalysts for organic reactions is of profound significance. During such processes, electrophilicity and nucleophilicity play vital roles in the activation of chemical bonds and ultimately speed up organic reactions. Herein, we demonstrate a new way to regulate the electro- and nucleophilicity of catalysts for organic transformations. Interface engineering in two-dimensional heteronanostructures triggered electron transfer across the interface. The catalyst was thus rendered more electropositive, which led to superior performance in Ullmann reactions. In the presence of the engineered 2D Cu2S/MoS2 heteronanostructure, the coupling of iodobenzene and para-chlorophenol gave the desired product in 92 % yield under mild conditions (100 °C). Furthermore, the catalyst exhibited excellent stability as well as high recyclability with a yield of 89 % after five cycles. We propose that interface engineering could be widely employed for the development of new catalysts for organic reactions.
Sun, Xu,Deng, Haitao,Zhu, Wenguang,Yu, Zhi,Wu, Changzheng,Xie, Yi
supporting information
p. 1704 - 1709
(2016/02/03)

Synthesis of copper nanoparticles supported on a microporous covalent triazine polymer: An efficient and reusable catalyst for O-arylation reaction
Copper nanoparticles were supported on a microporous covalent triazine polymer prepared by the Friedel-Crafts reaction (Cu@MCTP-1). The resulting material was characterized by powder X-ray diffraction, thermogravimetric analysis, N2 adsorption-desorption isotherms at 77 K, transmission electron microscopy, X-ray photoelectron spectroscopy, and inductively coupled plasma optical emission spectroscopy, and Cu particles with an average size of 3.0 nm and a BET total surface area of ca. 1002 m2 g-1 were obtained. Cu@MCTP-1 was evaluated as a heterogeneous catalyst for the Ullmann coupling of O-arylation over a series of aryl halides and phenols without employing expensive ligands or inert atmosphere, which produced an excellent yield of the corresponding diaryl ethers. The catalyst could be recovered by simple centrifugation and was reusable at least five times with only a slight decrease in catalytic activity.
Puthiaraj, Pillaiyar,Ahn, Wha-Seung
p. 1701 - 1709
(2016/04/05)

Four- and Sixfold Tandem-Domino Reactions Leading to Dimeric Tetrasubstituted Alkenes Suitable as Molecular Switches
A highly efficient palladium-catalyzed fourfold tandem-domino reaction consisting of two carbopalladation and two C-H-activation steps was developed for the synthesis of two types of tetrasubstituted alkenes 3 and 6 with intrinsic helical chirality starting from substrates 1 and 4, respectively. A sixfold tandem-domino reaction was also developed by including a Sonogashira reaction. 20 compounds with different substitution patterns were prepared with yields of up to 97%. Structure elucidation by X-ray crystallography confirmed helical chirality of the two alkene moieties. Photophysical investigations of some of the compounds showed pronounced switching properties through light-controlled changes of their stereochemical configuration.
Tietze, Lutz F.,Waldecker, Bernd,Ganapathy, Dhandapani,Eichhorst, Christoph,Lenzer, Thomas,Oum, Kawon,Reichmann, Sven O.,Stalke, Dietmar
p. 10317 - 10323
(2015/09/01)

Stimuli responsive reversible high contrast off-on fluorescence switching of simple aryl-ether amine based aggregation-induced enhanced emission materials
Aryl-ether amine based simple Schiff base molecules (1-5) showed aggregation induced enhanced emission (AIEE) in the solid state and rare stimuli responsive fluorescence off-on switching. The hard grounding of 1 resulted in irreversible fluorescence tuning from greenish-yellow to green. Heating or solvent exposure did not result in any fluorescence reversibility. Interestingly, the hard grounding of 2-5 led to the quenching of the solid state fluorescence and heating/solvent exposure produced clear bright fluorescence. Importantly, 2-5 exhibited reversible off-on fluorescence switching for several cycles without significant change in fluorescence intensity. It is noted that the turn-on fluorescence of 2-5 was slightly blue shifted compared to the initial solids. PXRD studies suggest that the switching of dark to bright fluorescence and vice versa of 2-5 is due to the reversible change of crystalline to amorphous phase and more planarization of the twisted structure. Single crystal analysis of 1 and 5 confirmed the twisted molecular conformation and strong intermolecular interactions in the crystal lattice, which led to AIEE by restricting free rotation and rigidifying the fluorophores in the solid state. The high contrast dark and bright fluorescence switching of 2-5 could be of potential interest in optoelectronic applications.
Kundu, Anu,Hariharan,Prabakaran,Moon, Dohyun,Anthony, Savarimuthu Philip
p. 98618 - 98625
(2015/12/05)

A family of ligand and anion dependent structurally diverse Cu(II) Schiff-base complexes and their catalytic efficacy in an O-arylation reaction in ethanolic media
Two nitrato bridged dinuclear systems [Cu2(L1)2(NO3)3]NO3·H2O (1) and [Cu2(L2)2(NO3)3]NO3·MeOH (2), five monomeric complexes viz. [Cu(L3)(NO3)]NO3 (3), [Cu(L4)(NO3)]NO3 (4), [Cu(L5)(NO3)]NO3 (5), [Cu(L6)(NO3)NO3] (7), [Cu(L7)(NO3)]NO3 (8) and one hetero bi-bridged (phenoxido and water) dinuclear complex [Cu2(L2)2(H2O)2](ClO4)4·4H2O (6) have been synthesized and characterized using several physicochemical methods (L1 = 1-(N-3-methoxysalicylideneimino)-ethane-2-piperazine, L2 = 1-(N-3-ethoxysalicylideneimino)-ethane-2-piperazine, L3 = 1-(N-4′-ethoxy-α-methylasalicylideneimino)-ethane-2-piperazine, L4 = 1-(N-5′-chloro-α-methylasalicylideneimino)-ethane-2-piperazine, L5 = 1-(N-5-chlorosalicylideneimino)-ethane-2-piperazine, L6 = 1-(N-4-methoxysalicylideneimino)-ethane-2-piperazine and L7 = 1-(N-4′-methoxy-α-methylasalicylideneimino)-ethane-2-piperazine). X-ray structural analysis showed that complexes 1 and 2 are discrete dinuclear species where the pentacoordinated metal centers are bridged through a nitrate ion. In 3, 4, 5 and 8 the monomeric copper center displays a square pyramidal geometry with a weak axial Cu-O bond. In 7, the monomeric copper center shows a distorted octahedral geometry with two coordinated nitrate anions. However, in 6 the two copper centers coordinate in different manners (one is square-pyramidal and the other is distorted octahedral) and are bridged through a phenoxido group and a water molecule. All complexes efficiently catalyze the C-O coupling reaction under homogeneous conditions at 80 °C to afford unsymmetrical diaryl ethers using nitroarenes to act as an excellent electrophile. Notably, the reaction is carried out in ethanol media which facilitates the avoidance of toxic wastes. Structurally diverse copper(ii) Schiff-base complexes have rarely been used systematically in catalytic C-O coupling reactions.
Maity, Tanmoy,Saha, Debraj,Bhunia, Susmita,Brand?o, Paula,Das, Soma,Koner, Subratanath
p. 82179 - 82191
(2015/10/12)

Ligand free copper-catalyzed heterogeneous O-arylation reaction under green condition
A highly porous Zn-based iso-reticular metal-organic framework (IRMOF-3) has been selected for covalent modification. Pyridine-2-aldehyde has been used to decorate the free amine group of IRMOF-3 in the porous matrix. Schiff base moiety thus generated has been availed to anchor copper(II) ions to prepare the desired catalyst that catalyzes O-arylation reactions heterogeneously under mild reaction conditions. Porous catalyst demonstrates size selectivity in products when various substrates undergo O-arylation with α and β-naphthol.
Maity, Tanmoy,Saha, Debraj,Das, Soma,Bhunia, Susmita,Koner, Subratanath
p. 141 - 148
(2014/12/10)

Chemoselective arylation of phenols with bromo-nitroarenes: Synthesis of nitro-biaryl-ols and their conversion into benzofurans and carbazoles
A series of electron withdrawing or donating group substituted phenols were chemoselectively arylated with various substituted bromo-nitroarenes using KOtBu at room temperature via an SNAr pathway. The synthesis of natural alkaloids (carbazoles), dibenzofurans, and a biaryl-indole was achieved from the synthesized nitro-biaryl-ols. This journal is the Partner Organisations 2014.
Kumar, Sangit,Kumar, Amit,Yadav, Abhimanyu,Verma, Ajay,Jana, Sadhan,Sattar, Moh.,Kumar, Shailesh,Prasad, Ch. Durga
supporting information
p. 9481 - 9484
(2014/08/18)

Synthesis of xanthones through the palladium-catalyzed carbonylation/C-H activation sequence
A series of xanthones with the dibenzo-γ-pyrone framework were synthesized through the palladium-catalyzed carbonylation/C-H activation sequence from the ortho diazonium salts of diaryl ethers in moderate to excellent yields. After screening the reaction condition, the optimal condition was 5 mol % tetrakis (triphenylphosphine) palladium (0) as the catalyst, potassium carbonate as the base, and toluene as the solvent in the presence of catalytic amount of tetrabutyl ammonium bromide under carbon monoxide atmosphere.
Xu, Yingmeng,Zhou, Jing,Zhang, Congcong,Chen, Ke,Zhang, Tao,Du, Zhenting
supporting information
p. 6432 - 6434
(2014/12/10)

Oxidation of aromatic amines into nitroarenes with m-CPBA
A versatile and highly efficient approach for the synthesis of nitroarenes from aromatic amine using m-CPBA has been developed. This oxidation reaction was operationally straightforward and proceeded to afford products in good isolated yields.
Liu, Jia,Li, Jue,Ren, Jiangmeng,Zeng, Bu-Bing
p. 1581 - 1584
(2014/03/21)

Palladium supported on zinc ferrite: An efficient catalyst for ligand free C-C and C-O cross coupling reactions
An efficient superparamagnetic Pd-ZnFe2O4 solid catalyst has been synthesized by loading Pd(0) species on zinc ferrite nanoparticles. Sonogashira cross couplings between terminal alkynes and aryl halides were achieved in the absence of any Cu co-catalyst. A Heck-Matsuda coupling reaction of structurally different aryldiazonium tetrafluoroborate substrates was preceded at 40 C in water. Cyanation of aryl halides was successfully done using K4[Fe(CN)6] as the cyanide source over Pd-ZnFe2O4. The catalyst was also employed for Ullmann type cross coupling reactions. Excellent yield of the products, reusability, and uncomplicated work-up make this catalyst efficient for C-C and C-O coupling reactions. Good yield of products, easy separation, and negligible leaching of Pd from the catalyst surface confirm the true heterogeneity in these catalytic reactions.
Singh, Abhilash S.,Shendage, Suresh S.,Nagarkar, Jayashree M.
p. 6319 - 6323
(2013/11/06)

Potassium tert-butoxide-mediated synthesis of unsymmetrical diaryl ethers, sulfides and selenides from aryl bromides
Potassium tert-butoxide mediated carbon-chalcogen C-E (E=O, S and Se) coupling reaction has been studied from aryl bromide and phenol/aryl disulfide/diselenide substrates. A series of unsymmetrical diaryl chalcogenides were accessed from aryl bromide and diaryl dichalcogenide precursors by using 2.5 equiv of potassium tert-butoxide in DMSO at 80 C. Unsymmetrical diaryl ethers were also obtained by using phenol precursors at 40-45 C. Aryl bromides with methyl, trifluoromethyl, methoxy and nitro substituents showed compatibility in the carbon-chalcogen bond forming reaction. 4-Methoxy, methyl, trifluoromethyl substituted bromobenzene substrates gave two regioisomers: 3-substituted and 4-substituted diaryl chalcogenides when reacted with phenols/diaryl disulfides/diselenides. Formation of two regioisomeric diaryl chalcogenides in the reaction mixture suggests that potassium tert-butoxide reacts with bromobenzene to produce benzyne intermediate, which subsequently reacts with diaryl dichalcogenides and finally give a regioisomeric mixture of 4-substituted and 3-substituted diaryl chalcogenides.
Kumar, Amit,Bhakuni, Bhagat Singh,Prasad, Ch. Durga,Kumar, Shailesh,Kumar, Sangit
p. 5383 - 5392
(2013/07/04)

2-Carbomethoxy-3-hydroxyquinoxaline-di-N-oxide as a novel ligand for the copper-catalyzed coupling reaction of phenols and aryl halides
2-Carbomethoxy-3-hydroxyquinoxaline-di-N-oxide was identified as an efficient novel ligand for the copper-catalyzed coupling of aryl halides with various phenols under mild conditions. The catalytic system shows great functional-group tolerance and excellent reactive selectivity.
Qiu, Yatao,Jia, Weijun,Yao, Zhiyi,Wu, Fanhong,Jiang, Sheng
p. 1502 - 1510
(2013/05/08)

Synthesis of aryl ethers from aromatic carboxylic acids
A silver/copper bimetallic catalyst system promotes the decarboxylative Chan-Evans-Lam alkoxylation of ortho-substituted aromatic carboxylate salts with tetraalkyl orthosilicates or triaryl borates. Non-ortho-substituted carboxylates are alkoxylated via an ortho-C-H-alkoxylation with concomitant cleavage of the carboxylate directing group via protodecarboxylation. This way, meta-substituted carboxylates are converted into para-substituted alkoxyarenes and vice versa. The combined processes provide a convenient synthetic entry to the important class of aromatic ethers from widely available carboxylic acids.
Bhadra, Sukalyan,Dzik, Wojciech I.,Goossen, Lukas J.
supporting information
p. 2387 - 2390
(2013/09/23)

Ligand-free solid supported palladium(0) nano/microparticles promoted C-O, C-S, and C-N cross coupling reaction
Ligand-free solid-supported nano and microparticles of Pd(0) (SS-Pd) were used as a heterogeneous catalyst in carbon-heteroatom bond formation reactions. Nitro substituted aryl halides reacted with oxygen, sulfur, and nitrogen nucleophiles to afford the corresponding products in good yields. A one-pot sequential cross coupling and nitro-reduction was also performed using the same SS-Pd catalyst to access amine substituted carbon-heteroatomic molecules. In addition, SS-Pd could be recycled up to seven runs without a significant loss of catalytic activity.
Bandna,Guha, Nitul Ranjan,Shil, Arun K.,Sharma, Dharminder,Das, Pralay
p. 5318 - 5322
(2012/10/30)

Synthesis of unsymmetrical biaryl ethers through nickel-promoted coupling of polyfluoroarenes with arylboronic acids and oxygen
Polyfluoro-substituted unsymmetrical biaryl ethers were synthesized via a novel Ni-catalyzed cross-coupling reaction of polyfluoroarenes with arylboronic acids and oxygen. The polyfluorinated arenes presumably captured the phenoxide intermediate efficiently, which made the oxygen-insertion proceed smoothly via the SNAr protocol. The 18O labeling experiment demonstrated that the oxygen introduced into unsymmetrical diaryl ether originated from very trace amounts of oxygen in the reaction system. A plausible mechanism was also suggested.
Zhang, Jian,Wu, Jingjing,Xiong, Yang,Cao, Song
supporting information; experimental part
p. 8553 - 8555
(2012/09/22)

Copper(II) trans-bis-(glycinato): An efficient heterogeneous catalyst for cross coupling of phenols with aryl halides
Copper(II) trans-bis-(glycinato) complex, easily prepared by the solid state reaction of copper(II) acetate and glycine (trans-[Cu(glyo) 2·H2O]) was found to be an efficient, recyclable, and high yielding catalyst for the Ullmann type synthesis of diaryl ethers via the cross coupling of phenols with aryl halides without using any additives at relatively low reaction temperature. The catalyst could easily be recovered by simple filtration and was reused for several runs with consistent catalytic activity.
Verma, Sanny,Kumar, Neeraj,Jain, Suman L.
experimental part
p. 4665 - 4668
(2012/09/05)

Exploration of the structure-activity relationship of the diaryl anilide class of ligands for translocator protein - Potential novel positron emitting tomography imaging agents
A series of novel ligands based on the diaryl anilide (DAA) class of translocator protein (TSPO) ligands was synthesised and evaluated as potential positron emitting tomography (PET) ligands for imaging TPSO in vivo. Fluorine-18 labelling of the molecules was achieved using direct radiolabelling or synthon based labelling approaches. Several of the ligands prepared have promising profiles as potential TSPO PET imaging ligands and will be evaluated further as potential clinical imaging agents.
Wadsworth, Harry,Jones, Paul A.,Chau, Wai-Fung,Durrant, Clare,Morisson-Iveson, Veronique,Passmore, Joanna,O'Shea, Dennis,Wynn, Duncan,Khan, Imtiaz,Black, Andrew,Avory, Michelle,Trigg, William
p. 5795 - 5800,6
(2020/07/30)

METHOD FOR PREPARATION OF MONONITRATED AROMATIC COMPOUNDS
The invention discloses a method for preparation of mononitrated aromatic compounds in a liquid-liquid biphasic solvent system with aqueous nitric acid as one phase and ionic liquids (ILs) as the second phase, wherein the nitric acid is continuously exchanged during the reaction, or the water, that is generated during the reaction, is removed by addition of NO2 and an oxidizing agent during the reaction.
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Page/Page column 25-26

(2012/12/13)

Decarboxylative etherification of aromatic carboxylic acids
Decarboxylative Chan-Evans-Lam-type couplings are presented as a new strategy for the regiospecific construction of diaryl and alkyl aryl ethers starting from easily available aromatic carboxylic acids. They allow converting various aromatic carboxylate salts into the corresponding aryl ethers by reaction with alkyl orthosilicates or aryl borates, under aerobic conditions in the presence of silver carbonate as the decarboxylation catalyst and copper acetate as the cross-coupling catalyst.
Bhadra, Sukalyan,Dzik, Wojciech I.,Goossen, Lukas J.
supporting information; experimental part
p. 9938 - 9941
(2012/08/08)

Ipso-nitration of arylboronic acids with bismuth nitrate and perdisulfate
An efficient and one pot synthetic method of ipso-nitration of arylboronic acids has been developed. The high efficiency, general applicability, and broader substrate scope including heterocycles and functional groups make this method advantageous. Due to its simplicity, we expect to find application of this method in synthesis.
Manna, Srimanta,Maity, Soham,Rana, Sujoy,Agasti, Soumitra,Maiti, Debabrata
supporting information; experimental part
p. 1736 - 1739
(2012/05/20)