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Keywords:

  • olefination;
  • aldehydes;
  • nucleophilic addition;
  • sulfones;
  • fluorine

Abstract

A highly stereoselective synthesis of tetrasubstituted monofluoroalkenes with aldehydes and fluorobis(phenylsulfonyl)methane (FBSM) in one pot has been developed. The reaction was amenable to para- and meta-substituted aryl aldehydes, 2-naphthaldehyde, and cinnamaldehyde, giving phenylsulfonyl-substituted monofluoroalkenes in 40%–86% yields with 98/2–99/1 Z/E ratios. The presence of the sulfonyl group enables the further transformation of the products into more useful monofluoroalkenes.