Synthesis of gem-Difluorinated 1,3-Dienes via Synergistic Cu/Pd-Catalyzed Borodifluorovinylation of Alkynes

Org Lett. 2022 Aug 19;24(32):5884-5889. doi: 10.1021/acs.orglett.2c01875. Epub 2022 Aug 4.

Abstract

gem-Difluoroalkenes (=CF2), which normally act as metabolically stable bioisosteres for carbonyl groups (C═O), are widely applied in agrochemicals and pharmaceuticals and are also used as building blocks in organic synthesis. Herein, an example of Cu/Pd-catalyzed borodifluorovinylation was achieved using alkynes, difluoroethylene bromide, and B2pin2 as chemical feedstocks, providing the corresponding conjugated gem-difluoroalkene scaffold with good functional group compatibility. Moreover, an array of fluorinated synthons can be obtained through further transformations.

MeSH terms

  • Alkynes*
  • Catalysis
  • Copper / chemistry
  • Molecular Structure
  • Palladium / chemistry
  • Polyenes

Substances

  • Alkynes
  • Polyenes
  • Palladium
  • Copper