Functionalized olefin cross-coupling to construct carbon–carbon bonds

Julian C. Lo, Jinghan Gui, Yuki Yabe, Chung-Mao Pan and Phil S. Baran ()
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Julian C. Lo: The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA
Jinghan Gui: The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA
Yuki Yabe: The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA
Chung-Mao Pan: The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA
Phil S. Baran: The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA

Nature, 2014, vol. 516, issue 7531, 343-348

Abstract: 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.

Date: 2014
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DOI: 10.1038/nature14006

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