Selective Fluoroalkylations With Fluorinated Sulfones, Sulfoxides, and Sulfides

Acc Chem Res. 2007 Oct;40(10):921-30. doi: 10.1021/ar700149s. Epub 2007 Aug 21.

Abstract

Efficient fluoroalkylations have been proven to be a highly useful strategy for the synthesis of bioactive fluorine-containing compounds and other materials. The design and use of a single category of reagents for multiple synthetic goals are much more attractive to preparative organic chemists. In this Account, we show how we have succeeded in the nucleophilic trifluoromethylation, difluoromethylation, difluoromethylenation, (phenylsulfonyl)difluoromethylation, (phenylthio)difluoromethylation, and monofluoromethylation as well as radical (phenylsulfonyl)difluoromethylation and electrophilic difluoromethylation by using fluorinated sulfones, sulfoxides, sulfides, or fluorinated sulfonium salts. The chemistry not only provides practically powerful synthetic methods, but the molecular design concept that we have developed may also be adopted to tackle other related chemical problems.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkylation
  • Fluorine / chemistry*
  • Indicators and Reagents / chemistry
  • Sulfides / chemistry*
  • Sulfones / chemistry*
  • Sulfoxides / chemistry*

Substances

  • Indicators and Reagents
  • Sulfides
  • Sulfones
  • Sulfoxides
  • Fluorine