4.8 Article

Merging Distal Alkynyl Migration and Photoredox Catalysis for Radical Trifluoromethylative Alkynylation of Unactivated Olefins

Journal

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 56, Issue 16, Pages 4545-4548

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201700413

Keywords

alkynes; olefins; photoredox catalysis; radicals; trifluoromethylation

Funding

  1. National Natural Science Foundation of China [21402134]
  2. Natural Science Foundation of Jiangsu Province [BK20140306]
  3. Priority Academic Program Development of Jiangsu Higher Education Institutions (PAPD)

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Disclosed herein is a novel, redox-neutral protocol for the visible-light-induced radical alkynylation of unactivated olefins. The intramolecular migration of an alkynyl group, by cleaving an inert C-C sigma bond, is realized for the first time. A wide range of synthetically useful trifluoroethylated linear alkynes are readily obtained under mild reaction conditions.

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