4.4 Article

Free radical (phenylsulfonyl)difluoromethylation of alkynes with PhSO2CF2I reagent: stereoselective preparation of PhSO2CF2- and CF2H-substituted alkenes

Journal

TETRAHEDRON
Volume 65, Issue 2, Pages 478-483

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2008.11.011

Keywords

Fluorine; Radical fluoroalkylation; (Phenylsulfonyl)difluoromethylation; Difluoromethyl

Funding

  1. National Natural Science Foundation of China [20502029, 20772144, 20825209]
  2. Shanghai Rising-Star Program [06QA14063]
  3. Chinese Academy of Sciences

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Stereoselective free radical (phenylsulfonyl)difluoromethylation of terminal alkynes with iododifluoromethyl phenyl sulfone (PhSO2CF2I) has been accomplished by using Et3B/air as an initiator. The obtained PhSO2CF2-substituted vinyl iodides, which can be further subjected to Suzuki coupling and Sonogashira coupling reactions, are useful precursors for the preparation of many structurally diverse PhSO2CF2- and CF2H-substituted alkenes. (C) 2008 Elsevier Ltd. All rights reserved.

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