Reações de acoplamento cruzado de organossilanos catalisadas por paládio: aspectos históricos, sintéticos e mecanísticos

Teixeira, Róbson Ricardo; Barbosa, Luiz C. A.; Piló-Veloso, Brasil Dorila

doi:10.1590/s0100-40422007000700038

Cited by 8 publications

(5 citation statements)

References 46 publications

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“…1 The use of silanes as a protecting group for oxygen functionalities is, of course, well documented, and much interest has focused on their use in low cost, non-toxic routes to the formation of carbon-carbon bonds. These include Sakurai allylations, 2 fluoride mediated Hiyama cross-coupling, 3 and the fluorine-free Denmark-Hiyama cross-coupling variation 4 and a number of copper mediated oxygen-carbon silicon migrations have been reported in the last decade. 5 They have also found use in the formation of carbon-oxygen bonds through Tamao-Fleming oxidation 6 and the development of an epoxidation-oxidation reaction sequence.…”

Section: Introductionmentioning

confidence: 99%

“…Trost and coworkers have investigated this reaction extensively, firstly using a cyclopentadienyl ruthenium complex to perform the desired hydrosilylation with moderate stereoselectivity. 22 Further investigation led to the development of a highly active and selective cationic catalyst, [Cp*Ru(MeCN) 3 ]PF 6 , which gives the α-vinylsilane in a >20 : 1 ratio. 23 The Lewis acid catalysed hydrosilylation of a range of alkynes with diverse functionality, as developed by Yamamoto, [24][25][26][27] also affords the α-isomer as a single product, although this method is still in its infancy.…”

Section: Introductionmentioning

confidence: 99%

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Platinum catalysed hydrosilylation of propargylic alcohols

et al. 2013

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A facile and user-friendly protocol has been developed for the selective synthesis of E-vinyl silanes derived from propargylic alcohols using a PtCl2/XPhos catalyst system. The reaction is generally high yielding and provides a single regioisomer at the β-position with E-alkene geometry. The reaction is extremely tolerant of functionality and has a wide scope of reactivity both in terms of alkynes and silanes used. The catalyst loading has been investigated and it is found that good reactivity is observed at extremely low catalyst loadings. This methodology has also been extended to a one-pot hydrosilylation Denmark-Hiyama coupling.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Platinum catalysed hydrosilylation of propargylic alcohols

et al. 2013

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“…O Esquema 1 generaliza estas etapas, para uma reação catalisada por paládio (0). 13,14 Rev. Virtual Quim.…”

Section: Novos Sistemas Catalíticosunclassified

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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“…44 As reações de acoplamentos cruzados são amplamente utilizadas nas sínteses de moléculas de alto e baixo peso molecular com ampla possibilidade de aplicação industrial de preparação de novos fármacos contra o câncer e AIDS e defensivos agrícolas, dentre outros. 45 Além disso, a síntese total de moléculas com estruturas complexas pode ser obtida através de um número reduzido de etapas sintéticas, com elevada seletividade.…”

Section: Reações De Acoplamento Cruzadounclassified

An Overview of the Different Types of Catalysts in Organic Synthesis

Dias¹,

Ferreira²,

Cunha³

2012

Revista Virtual De Química

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Abstract:Since the mid-twentieth century, by economic and environmental factors, many researchers and some industries are investing in the development of syntheses and technologies that are environmentally friendly, producing less toxic waste and saving energy. Furthermore, the use of renewable raw materials, biomass and the development of asymmetric methods that provide products with high yields and selectivities becomes a major challenge for researchers in various fields that employ the catalytic process. This paper describes the importance of catalysis in organic synthesis of complex molecules, especially for the pharmaceutical and fine chemicals industries. Indeed, the industrial revolution caused by catalysis in different sectors such as petrochemicals, plastics, paper, among others, also became the subject of interest of this review.Keywords: Homogeneous catalysis; heterogeneous catalysis; biocatalysis; organocatalysis. ResumoDesde meados do século XX, por razões econômicas e ambientais, diversos pesquisadores e algumas indústrias investem no desenvolvimento de tecnologias sintéticas que sejam ambientalmente favoráveis, gerando menos resíduos tóxicos e com economia de energia. Além disso, os processos catalíticos e biocatalíticos associados ao uso de biomassas renováveis são de fundamental importância para a produção de matérias-primas quirais e aquirais com altos rendimentos e elevadas seletividades. Esse conjunto de paradigmas é um dos grandes desafios da atualidade para os pesquisadores nos diversos ramos da síntese orgânica.Este trabalho descreve a importância da catálise e da biocatálise na síntese orgânica de moléculas complexas, destacando-se os setores de química fina e fármacos. Além disso, a utilização crescente dos diversos processos catalíticos em diferentes setores industriais, tais como petroquímico, de papel e celulose, plásticos, e muitos outros também são assuntos de interesse desse trabalho de revisão.Palavras-chave: Catálise homogênea; catálise heterogênea; biocatálise; organocatálise.

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Reações de acoplamento cruzado de organossilanos catalisadas por paládio: aspectos históricos, sintéticos e mecanísticos

Cited by 8 publications

References 46 publications

Platinum catalysed hydrosilylation of propargylic alcohols

Platinum catalysed hydrosilylation of propargylic alcohols

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

An Overview of the Different Types of Catalysts in Organic Synthesis

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