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Functionalized olefin cross-coupling to construct carbon-carbon bonds

机译：功能化烯烃交叉偶联以构建碳-碳键

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摘要

这篇论文报告了一个新型碳—碳键形成反应的研究成功，该反应使得人们能够简单地生成以前要么不可能获得、要么难以获得的分子。该反应利用一种简单的铁催化剂和一种廉价的硅烷通过异原子取代的烯烃与缺电子烯烃之间的相互作用来形成高度取代的碳一碳键。作者介绍了超过60个这一反应的例子，覆盖一系列不同的基质。这一反应对于包括聚合物、染料和药物及半导体在内的有机化合物的设计有参考意义。%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.
机译：这篇论文报告了一个新型碳—碳键形成反应的研究成功，该反应使得人们能够简单地生成以前要么不可能获得、要么难以获得的分子。该反应利用一种简单的铁催化剂和一种廉价的硅烷通过异原子取代的烯烃与缺电子烯烃之间的相互作用来形成高度取代的碳一碳键。作者介绍了超过60个这一反应的例子，覆盖一系列不同的基质。这一反应对于包括聚合物、染料和药物及半导体在内的有机化合物的设计有参考意义。%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.

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  • 来源
    《Nature》 |2014年第7531期|343-348B1|共7页
  • 作者

    Julian C. Lo; Jinghan Gui; Yuki Yabe; Chung-Mao Pan; Phil S. Baran;

  • 作者单位

    Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA;

    Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA;

    Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA;

    Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA;

    Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA;

  • 收录信息 美国《科学引文索引》(SCI);美国《工程索引》(EI);美国《生物学医学文摘》(MEDLINE);美国《化学文摘》(CA);
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