4.8 Article

Stereocontrolled Access to Unsymmetrical 1,1-Diaryl-2-fluoroethenes

Journal

ORGANIC LETTERS
Volume 11, Issue 23, Pages 5406-5409

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol9022672

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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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A simple and effective method for stereocontrolled preparation of 1,1-diaryl-2-fluoroethenes is reported. First, 1-aryl-1-bromo-2-fluoroethenes are generated using an addition/elimination reaction of hydride to silylated beta,beta-difluorostyrene derivatives followed by a bromination/desilicobromination reaction. Subsequent Suzuki-Miyaura coupling with a variety of boronic acids gives access to the desired 1,1-diaryl-2-fluoroethenes.

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