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Functionalized olefin cross-coupling to construct carbon-carbon bonds

Academic Article
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Overview

related to degree

  • Lo, Julian Castro, Ph.D. in Chemistry, Scripps Research 2012 - 2017

authors

  • Lo, Julian Castro
  • Gui, J.
  • Yabe, Y.
  • Pan, C. M.
  • Baran, Phil

publication date

  • 2014

journal

  • Nature  Journal

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.

subject areas

  • Alkenes
  • Carbon
  • Chemistry Techniques, Synthetic
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Identity

PubMed Central ID

  • PMC4271735

International Standard Serial Number (ISSN)

  • 0028-0836

Digital Object Identifier (DOI)

  • 10.1038/nature14006

PubMed ID

  • 25519131
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Additional Document Info

start page

  • 343

end page

  • 348

volume

  • 516

issue

  • 7531

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