Negishi cross-coupling of organotellurium compounds: synthesis of biaryls, aryl-, and diaryl acetylenes

Stefani, Hélio A.; Pena, Jesus M.; Manarin, Flávia; Ando, Rômulo Augusto; Leal, Daiana M.; Petragnani, Nicola

doi:10.1016/j.tetlet.2011.06.025

Cited by 32 publications

(12 citation statements)

References 27 publications

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“…Tellurium/metal‐exchange reactions have attracted the interest of chemists owing to the special regio‐ and stereoselectivity properties that are unique to tellurium species. In this sense, cross‐coupling reactions such as Suzuki–Miyaura,14 Sonogashira,15 Negishi,16 Heck17 and homo coupling reactions18 have attracted attention. Moreover, unnamed reactions involving various metals and non‐metals such as magnesium,19 zinc,20 aluminum,21 tin,22 phosphorus,23 iodine,24 and a Te/halide25 exchange process have been developed.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of 5‐Organotellanyl‐1H‐1,2,3‐triazoles: Functionalization of the 5‐Position Scaffold by the Sonogashira Cross‐Coupling Reaction

et al. 2013

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An efficient synthesis of 5‐organotellanyl‐1H‐1,2,3‐triazole compounds was accomplished through [3+2] cycloaddition reaction of organic azides and (organotellanyl)alkynes. Additionally, 5‐organotellanyl‐1H‐1,2,3‐triazoles were readily functionalized at the 5‐position by using a Sonogashira cross‐coupling reaction, leading to highly functionalised triazoles. The regiochemistry of the products was assessed by two‐dimensional NMR spectroscopic experiments and X‐ray crystallography.

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Section: Introductionmentioning

confidence: 99%

Synthesis of 5‐Organotellanyl‐1H‐1,2,3‐triazoles: Functionalization of the 5‐Position Scaffold by the Sonogashira Cross‐Coupling Reaction

et al. 2013

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“…It was also reported in 2011 that diaryl tellurides could be coupled with organozincs using palladium and copper catalysts [178]. The products were obtained in moderate yields.…”

Section: Negishi-baba Cross-couplingmentioning

confidence: 73%

Cross‐Coupling Arylations: Precedents and Rapid HistoricalReview of the Field

2014

Catalytic Arylation Methods

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“…43 Okamoto e seu grupo de pesquisas descreveram a síntese de benzimidazol [ Os autores demonstraram que organotelúrios são capazes de transferir os dois núcleos aromáticos para a formação do produto de acoplamento, constituindo-se desta forma em eficientes eletrófilos frente à reação de Negishi. 53 Ainda com foco na reação de Negishi, Knochel e colaboradores demonstraram que eletrófilos contendo a função amida ou sulfonamida podem ser compatíveis em reações com organozincos. Até então, na literatura existiam relatos apenas da aplicação de ésteres e de ácidos borônicos como substratos capazes de reagir com substratos amídicos sem a necessidade proteção prévia.…”

Section: Uso De Micro-ondasunclassified

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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Negishi cross-coupling of organotellurium compounds: synthesis of biaryls, aryl-, and diaryl acetylenes

Cited by 32 publications

References 27 publications

Synthesis of 5‐Organotellanyl‐1H‐1,2,3‐triazoles: Functionalization of the 5‐Position Scaffold by the Sonogashira Cross‐Coupling Reaction

Synthesis of 5‐Organotellanyl‐1H‐1,2,3‐triazoles: Functionalization of the 5‐Position Scaffold by the Sonogashira Cross‐Coupling Reaction

Cross‐Coupling Arylations: Precedents and Rapid HistoricalReview of the Field

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

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Negishi cross-coupling of organotellurium compounds: synthesis of biaryls, aryl-, and diaryl acetylenes

Cited by 32 publications

References 27 publications

Synthesis of 5‐Organotellanyl‐1H‐1,2,3‐tri­azoles: Functionalization of the 5‐Position Scaffold by the Sonogashira Cross‐Coupling Reaction

Synthesis of 5‐Organotellanyl‐1H‐1,2,3‐tri­azoles: Functionalization of the 5‐Position Scaffold by the Sonogashira Cross‐Coupling Reaction

Cross‐Coupling Arylations: Precedents and Rapid HistoricalReview of the Field

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

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Product

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Synthesis of 5‐Organotellanyl‐1H‐1,2,3‐triazoles: Functionalization of the 5‐Position Scaffold by the Sonogashira Cross‐Coupling Reaction

Synthesis of 5‐Organotellanyl‐1H‐1,2,3‐triazoles: Functionalization of the 5‐Position Scaffold by the Sonogashira Cross‐Coupling Reaction