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Functionalized olefin cross-coupling to construct carbon-carbon bonds.

ABSTRACT: Carbon-carbon (C-C) bonds form the backbone of many important molecules, including polymers, dyes and pharmaceutical agents. The development of new methods to create these essential connections in a rapid and practical fashion has been the focus of numerous organic chemists. This endeavour relies heavily on the ability to form C-C bonds in the presence of sensitive functional groups and congested structural environments. Here we report a chemical transformation that allows the facile construction of highly substituted and uniquely functionalized C-C bonds. Using a simple iron catalyst, an inexpensive silane and a benign solvent under ambient atmosphere, heteroatom-substituted olefins are easily reacted with electron-deficient olefins to create molecular architectures that were previously difficult or impossible to access. More than 60 examples are presented with a wide array of substrates, demonstrating the chemoselectivity and mildness of this simple reaction.

SUBMITTER: Lo JC

PROVIDER: S-EPMC4271735 | biostudies-literature | 2014 Dec

REPOSITORIES: biostudies-literature

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Functionalized olefin cross-coupling to construct carbon-carbon bonds.

Lo Julian C JC Gui Jinghan J Yabe Yuki Y Pan Chung-Mao CM Baran Phil S PS

Nature 20141201 7531

Carbon-carbon (C-C) bonds form the backbone of many important molecules, including polymers, dyes and pharmaceutical agents. The development of new methods to create these essential connections in a rapid and practical fashion has been the focus of numerous organic chemists. This endeavour relies heavily on the ability to form C-C bonds in the presence of sensitive functional groups and congested structural environments. Here we report a chemical transformation that allows the facile constructio ...[more]

PMID: 25519131

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