Deuteriodifluoromethylation and gem-Difluoroalkenylation of Aldehydes Using ClCF2H in Continuous Flow

Wai Chung Fu, Timothy F. Jamison

Research output: Journal article publicationJournal articleAcademic researchpeer-review

9 Citations (Scopus)

Abstract

The deuteriodifluoromethyl group (CF2D) represents a challenging functional group due to difficult deuterium incorporation and unavailability of precursor reagents. Herein, we report the use of chlorodifluoromethane (ClCF2H) gas in the continuous flow deuteriodifluoromethylation and gem-difluoroalkenylation of aldehydes. Mechanistic studies revealed that the difluorinated oxaphosphetane (OPA) intermediate can proceed via alkaline hydrolysis in the presence of D2O to provide α-deuteriodifluoromethylated benzyl alcohols or undergo a retro [2+2] cycloaddition under thermal conditions to provide the gem-difluoroalkenylated product.

Original languageEnglish
Pages (from-to)13885-13890
Number of pages6
JournalAngewandte Chemie - International Edition
Volume59
Issue number33
DOIs
Publication statusPublished - 10 Aug 2020
Externally publishedYes

Keywords

  • chlorodifluoromethane
  • continuous flow
  • deuteration
  • difluoromethylation
  • gem-difluoroalkene

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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