Efficient Negishi Coupling Reactions of Aryl Chlorides Catalyzed by Binuclear and Mononuclear Nickel−N-Heterocyclic Carbene Complexes

The tricyclohexylphosphane adduct of cyclopalladated ferrocenylimine I exhibited high catalytic activity in the one‐pot borylation/Suzuki–Miyaura coupling (BSC) reaction with low catalyst loading (2 mol‐%). Various biaryls were obtained in good to excellent yields for 37 examples. This process was applied to aryl and heteroaryl halides (Br and Cl) containing a variety of functional groups and did not require an excess amount of phosphane ligand and the addition of the palladium catalyst in the second step.

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“…[30] Purified by flash chromatography on silica gel (ethyl acetate/petroleum ether, 1:30) to afford a white solid (90 mg, 91 %), m.p. 35-36°C.…”

Section: -Methoxy-4ј-(trifluoromethyl)biphenyl (30d)mentioning

confidence: 99%

Synthesis of Biaryls through a One‐Pot Tandem Borylation/Suzuki–Miyaura Cross‐Coupling Reaction Catalyzed by a Palladacycle

Wang

Cui

Li³

et al. 2011

Eur J Org Chem

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“…Eles estudaram a influência de quatro complexos mononucleares (1a-d) e de três binucleares (2a-c), na reação entre clorobenzeno (3) e cloreto de p-toluilzinco (4) (Esquema 2). 15 Rev. Virtual Quim.…”

Section: Novos Complexos E Ligantesunclassified

“…2| |494-550| Esquema 2. Eficiência de diferentes complexos de níquel (II) (1a-d e 2a-c) na reação entre o clorobenzeno (3) o cloreto de p-toluilzinco (4) 15 Dentre os quatro complexos mononucleares, 1a mostrou-se o mais eficiente. Os autores justificaram este resultado pela facilidade de dissociação dos grupos piridínicos presentes neste complexo, uma vez que os quatro anéis do sistema bis(piridil-imidazol-ilidenil)-metano permanecem coplanares entre si junto ao íon de níquel (II) central, o que faz com que a tensão interna do sistema seja maior que nos outros complexos mononucleares (1b-d).…”

Section: Novos Complexos E Ligantesunclassified

C-C Cross-Coupling: New Methodologies, Applications and Discoveries over the Last Few Years

Batalha¹,

Sagrillo²,

Gama³

2014

Revista Virtual De Química

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Abstract:The possibility of obtaining new C-C bonds from the transition metals mediated catalysis, has represented a major advance in Organic Synthesis and correlated areas such as Chemistry of Natural Products and Medicinal Chemistry, since synthetically unreachable molecules could be obtained in an efficient and chemosselective way, from simple reactants. The cross-coupling reactions, as some of these processes are called, have gained prominence since the original publications of Suzuki-Miyaura, Kumada-Tamao-Corriu, Mizoroki-Heck, Sonogashira, Stille -during the 1970's -and Hiyama -in 1988. Since then numerous efforts are made by scientists around the world in order to not only understand better these processes, but also develop new catalytic systems with more efficiency and applicable to a wider range of substrates and the concepts of Green Chemistry. This work aims to expose some of the advances published by scientists around the world, in the last six years, based on this theme.Keywords: Cross coupling; new substrates; microwaves; palladium; gold. ResumoA possibilidade de se obter novas ligações C-C, a partir de reações de catálise mediadas por metais de transição, tem representado um grande avanço em Síntese Orgânica e áreas correlatas como a Química de Produtos Naturais e a Química Medicinal, uma vez que moléculas até então inalcançáveis sinteticamente puderam ser obtidas de forma eficiente e quimiosseletiva a partir de reagentes simples. As reações de acoplamento cruzado, como alguns desses processos são chamados, têm ganhado destaque desde as publicações originais de Suzuki-Miyaura, Kumada-Tamao-Corriu, Mizoroki-Heck, Sonogashira, Stille -durante a década de 1970 -e de Hiyama -em 1988. Desde então são numerosos os esforços feitos por cientistas do mundo todo no sentido de não apenas entender melhor tais processos, mas também desenvolver novos sistemas catalíticos mais eficientes e aplicáveis a uma maior variedade de substratos e aos conceitos da Química Verde. Este trabalho objetiva expor alguns dos avanços publicados por cientistas ao redor do mundo, nos últimos seis anos, com base neste tema.

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“…The cross-coupling between arylzincs and electron-poor aryl chlorides occurs with good yields in THF at rt in the presence of Ni(acac) 2 (5 mol%) [199].…”

Section: Nickel-catalyzed Cross-coupling Reactionsmentioning

confidence: 99%

Carbon–Carbon Bond Forming Reactions Mediated by Organozinc Reagents

Chemla

Ferreira

Jackowski

et al. 2013

Metal‐Catalyzed Cross‐Coupling Reactions and More

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Efficient Negishi Coupling Reactions of Aryl Chlorides Catalyzed by Binuclear and Mononuclear Nickel−N-Heterocyclic Carbene Complexes

Cited by 97 publications

References 71 publications

Synthesis of Biaryls through a One‐Pot Tandem Borylation/Suzuki–Miyaura Cross‐Coupling Reaction Catalyzed by a Palladacycle

Synthesis of Biaryls through a One‐Pot Tandem Borylation/Suzuki–Miyaura Cross‐Coupling Reaction Catalyzed by a Palladacycle

C-C Cross-Coupling: New Methodologies, Applications and Discoveries over the Last Few Years

Carbon–Carbon Bond Forming Reactions Mediated by Organozinc Reagents

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