4.8 Article

Stereocontrolled Approach to Bromofluoroalkenes and Their Use for the Synthesis of Tri- and Tetrasubstituted Fluoroalkenes

Journal

ORGANIC LETTERS
Volume 11, Issue 3, Pages 681-684

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol8027412

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Funding

  1. Canada Research Chair Program
  2. Natural Sciences and Engineering Research Council of Canada
  3. Canada Foundation for Innovation
  4. Merck Frosst Centre for Therapeutic Research
  5. Fonds de recherche sur la nature et les technologies
  6. Universite Laval

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An addition/elimination reaction of organolithium reagents to silylated beta,beta-difluorostyrene derivatives followed by a bromination/desilicobromination reaction provides a simple and effective synthetic approach to a wide range of bromofluoroalkenes (up to >97/3). In addition, the bromofluoroalkenes can be used in Pd-catalyzed transformations giving access to both tri- and tetrasubstituted fluoroalkenes.

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