gem-Difluoroalkenylation of aldehydes and ketones with bis(difluoromethyl)triphenylphosphorane under operationally simple conditions

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Abstract

Aldehydes and ketones were converted to gem-difluoroalkenes under straightforward conditions utilizing bis(difluoromethyl)triphenylphosphorane (PPh3(CF2H)2, 1) as the reagent. This approach eliminates the need for pre-formed phosphorus ylides and extra additives. By heating, the reagent directly generates a difluoromethylene ylide intermediate, facilitating the transformation of aldehydes and less hindered ketones into gem-difluoroalkenes with yields ranging from moderate to excellent. The method offers simple reaction conditions, wide substrate compatibility, and promising prospects for scalability.

Original languageEnglish
Article number134461
JournalTetrahedron
Volume173
DOIs
StatePublished - 1 Mar 2025

Keywords

  • Bis(difluoromethyl)triphenylphosphorane
  • Wittig reaction
  • gem-Difluoroalkenes

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