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

Functionalized olefin cross-coupling to construct carbon-carbon bonds.
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DOI:
10.1038/nature14006
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发表时间:
2014-12-18
期刊:
影响因子:
64.8
通讯作者:
Baran, Phil S.
Baran, Phil S.
中科院分区:
综合性期刊1区
文献类型:
--
作者:
Lo, Julian C.;Gui, Jinghan;Yabe, Yuki;Pan, Chung-Mao;Baran, Phil S.

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碳-碳(C-C)键构成了许多重要分子的骨架,包括聚合物、染料和药剂。发展新方法以快速和实用的方式创造这些基本联系一直是许多有机化学家关注的焦点。这种努力在很大程度上依赖于在敏感官能团和拥挤的结构环境中形成C-C键的能力。在这里,我们报告了一种全新的化学转化,可以方便地构建高度取代和独特功能化的C-C键。使用简单的铁催化剂、廉价的硅烷和环境气氛下的良性溶剂,杂原子取代烯烃很容易与缺电子烯烃结合,形成以前难以或不可能获得的分子结构。超过60个例子提出了广泛的底物阵列,展示了独特的化学选择性和温和的这个简单的反应。
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 endeavor heavily relies on the ability to form C–C bonds in the presence of sensitive functional groups and congested structural environments. Here we report a fundamentally new chemical transformation that allows for 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 an ambient atmosphere, heteroatom-substituted olefins are easily merged with electron-deficient olefins to create molecular architectures that were previously difficult or impossible to access. More than sixty examples are presented with a wide array of substrates, demonstrating the unique chemoselectivity and mildness of this simple reaction.
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