2050-67-1Relevant articles and documents
Base- and phosphine-free palladium-catalyzed homocoupling of arylboronic acid derivatives under air
Yamamoto, Yoshihiko,Suzuki, Ryo,Hattori, Kozo,Nishiyama, Hisao
, p. 1027 - 1030 (2006)
In the presence of a catalytic amount of Pd(OAc)2, various arylboronic acids underwent homocoupling in MeOH at ambient temperature under air to give rise to symmetrical biaryls. The homocoupling of arylboronic acids was also carried out using polyurea-encapsulated Pd(OAc)2 as a recyclable catalyst. Georg Thieme Verlag Stuttgart.
A facile method for the dechlorination of mono- and dichlorobiphenyls using Raney Ni-Al alloy in dilute aqueous solutions of alkali hydroxides or alkali metal carbonates
Liu, Guo-Bin,Tashiro, Masashi,Thiemann, Thies
, p. 2497 - 2505 (2009)
Raney Ni-Al alloy in a dilute aqueous alkaline solution of NaOH, KOH, CsOH, LiOH, or Ca(OH) 2 or of alkali metal carbonates such as Na2CO3, K2CO3 becomes a very powerful reducing agent and dechlorinates the polychlorobiphenyl(PCB) congeners mono- and dichlorobiphenyls effectively to afford biphenyl and/or phenylcyclohexane, respectively. The reactions are run under mild conditions without the use of organic solvents. The reductive dechlorination of dichlorobiphenyls with a Raney Ni-Al alloy under ultrasonication was investigated, also.
Rhodium-catalyzed oxidative homocoupling of boronic acids
Vogler, Thomas,Studer, Armido
, p. 1963 - 1967 (2008)
Oxidative homocoupling of aryl- and alkenylboronic acids was achieved with Wilkinson's catalyst. Commercially available 2,2,6,6-tetramethylpiperidine-N- oxyl radical (TEMPO) was used as a stoichiometric oxidant.
Synthesis of new 2-arylbenzo[b]thiophenes using 'Heck-type' technology
Fournier Dit Chabert, Jérémie,Gozzi, Christel,Lemaire, Marc
, p. 1829 - 1833 (2002)
Direct 3-substituted benzothiophene arylation using a Heck-type reaction with Pd(OAc)2/n-Bu4NBr as a catalytic system is reported. This reaction was found to perform relatively fast whatever the electron-donating or the electron-withdrawing group at position 3. We also extended this reaction to several aromatic halides, such as benzene, naphthalene and pyridine derivatives, synthesising new 2-arylbenzo[b]thiophenes in moderate to good yields.
Cobalt-catalyzed cross-coupling reactions of aryl- And alkylaluminum derivatives with (hetero)aryl and alkyl bromides
Dilauro, Giuseppe,Messa, Francesco,Bona, Fabio,Perrone, Serena,Salomone, Antonio
supporting information, p. 10564 - 10567 (2021/10/19)
A simple cobalt complex, such as Co(phen)Cl2, turned out to be a highly efficient and cheap precatalyst for a host of cross-coupling reactions involving aromatic and aliphatic organoaluminum reagents with aryl, heteroaryl and alkyl bromides. New C(sp2)-C(sp2) and C(sp2)-C(sp3) bonds were formed in good to excellent yields and with high chemoselectivity, under mild reaction conditions.
Porphyrin n-pincer pd(Ii)-complexes in water: A base-free and nature-inspired protocol for the oxidative self-coupling of potassium aryltrifluoroborates in open-air
Prasad, Sana Siva,Naidu, Bandameeda Ramesh,Hanafiah, Marlia M.,Lakshmidevi, Jangam,Marella, Ravi Kumar,Lakkaboyana, Sivarama Krishna,Venkateswarlu, Katta
, (2021/09/13)
Metalloporphyrins (and porphyrins) are well known as pigments of life in nature, since representatives of this group include chlorophylls (Mg-porphyrins) and heme (Fe-porphyrins). Hence, the construction of chemistry based on these substances can be based on the imitation of biological systems. Inspired by nature, in this article we present the preparation of five different porphyrin, meso-tetraphenylporphyrin (TPP), meso-tetra(p-anisyl)porphyrin (TpAP), tetra-sodium meso-tetra(p-sulfonatophenyl)porphyrin (TSTpSPP), meso-tetra(m-hydroxyphenyl)porphyrin (TmHPP), and meso-tetra(m-carboxyphenyl)porphyrin (TmCPP) as well as their N-pincer Pd(II)-complexes such as Pd(II)-meso-tetraphenylporphyrin (PdTPP), Pd(II)-meso-tetra(p-anisyl)porphyrin (PdTpAP), Pd(II)-tetrasodium meso-tetra(p-sulfonatophenyl)porphyrin (PdTSTpSPP), Pd(II)-meso-tetra(m-hydroxyphenyl)porphyrin (PdTmHPP), and Pd(II)-meso-tetra(m-carboxyphenyl)porphyrin (PdTmCPP). These porphyrin N-pincer Pd(II)-complexes were studied and found to be effective in the base-free self-coupling reactions of potassium aryltrifluoroborates (PATFBs) in water at ambient conditions. The catalysts and the products (symmetrical biaryls) were characterized using their spectral data. The high yields of the biaryls, the bio-mimicking conditions, good substrate feasibility, evading the use of base, easy preparation and handling of catalysts, and the application of aqueous media, all make this protocol very attractive from a sustainability and cost-effective standpoint.
Synthesis of biaryl compounds via Suzuki homocoupling reactions catalyzed by metal organic frameworks encapsulated with palladium nanoparticles
Bao, Yan-Sai,Cui, Xin-Yu,Han, Zheng-Bo,Li, Xin,Tang, Hong,Yang, Ming,Zhang, Yu-Yang,Zhao, Kun,Zhou, Mei-Li
, (2020/12/17)
Heterogeneous homocoupling reactions of phenylboronic acids were greatly accelerated via Suzuki homocoupling reactions. In this work, a tandem route was designed which firstly one part of phenylboronic acids reacted with iodine to form iodobenzenes, then another part of phenylboronic acids coupled with iodobenzenes to produce biaryl compounds. The tandem reaction were catalyzed by a bifunctional heterogeneous catalyst of metal organic frameworks encapsulated with palladium nanoparticles (Pd?MOFs). This strategy for forming symmetric C-C bond between benzene rings has obvious advantages such as high efficiency, easy separation, good recyclability and no addition of toxic halogenated benzene.
Pd-catalyzed oxidative homocoupling of arylboronic acids in WEPA: A sustainable access to symmetrical biaryls under added base and ligand-free ambient conditions
Appa, Rama Moorthy,Lakshmidevi, Jangam,Naidu, Bandameeda Ramesh,Venkateswarlu, Katta
, (2021/01/11)
Symmetrical and unsymmetrical biaryls comprises a diverse class of biologically eloquent organic compounds. We herein report, a quick and eco-friendly protocol for the synthesis of biaryls by an oxidative (aerobic) homocoupling of arylboronic acids (ABAs) using Pd(OAc)2 in water extract of pomogranate ash (WEPA) as an efficient agro-waste(bio)-derived aqueous (basic) media. The reactions were executed at ambient aerobic conditions in the absence of external base and ligand to result symmetrical biaryls in excellent yields. The use of renewable media with an effective exploitation of waste, short reaction times, excellent yields of products, easy separation of the products, unnecessating the external base, oxidant, ligand or volatile organic solvents and ambient reaction conditions are the vital insights of the present protocol.
Sustainable Synthesis of Biaryls Using Silica Supported Ferrocene Appended N-Heterocyclic Carbene-Palladium Complex
Khanapure, Sharanabasappa,Pore, Dattaprasad,Jagadale, Megha,Patil, Vaishali,Rashinkar, Gajanan
, p. 2237 - 2249 (2021/01/11)
Abstract: A novel silica supported ferrocene appended N-heterocyclic carbene-palladium complex (SilFemBenzNHC@Pd) has been prepared and characterized by using fourier transform infrared (FT-IR), fourier transform Raman (FT-Raman), X-ray photoelectron spectroscopy (XPS), scanning electron microscopy (SEM), thermogravimetric analysis (TGA) and energy dispersive X-ray analysis (EDX). This novel complex served as a robust heterogeneous catalyst for the synthesis of biaryls via homocoupling of aryl boronic acids under base-free conditions in water. Recyclability experiments were executed successfully for six successive runs. Graphic Abstract: [Figure not available: see fulltext.]
Ligand and Base Free Synthesis of Biaryls from Aryl Halides in Aqueous Media with Recyclable Ti0.97Pd0.03O1.97 Catalyst
Prasanna,Bhat, Shrikanth K.,Usha,Hegde
, p. 3313 - 3322 (2021/03/04)
Abstract: Facile protocol for the synthesis of biaryls from aryl halides in presence of magnesium metal without prior formation of organometallic intermediate has been exploited. Irrespective of aqueous medium, Ti0.97Pd0.03O1.97 catalyst supports C–C bond formation reaction in presence of metals rather than dehalogenation without any additives. Homocoupling of 16 different aryl halides furnished corresponding biphenyls in good yield with better functional group tolerance. The recovery of the catalyst was carried out by employing catalyst coated cordierite monolith up to 7th cycle with high yields. A new approach for the cross-coupling reaction is also attempted. Graphic Abstract: [Figure not available: see fulltext.]
