Transition-Metal-Free Carbonyl Reduction and Hydrodefluorination of β-Trifluoromethyl Enones with Hydrosilanes: Synthesis of gem-Difluorovinyl Alcohols

Peng Yuan Zhang, Ya Fei Hu, Jia Hao Chu, Ren Jun Zheng, Mengtao Ma, Zhi Liang Shen, Xue Qiang Chu

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2 Scopus citations

Abstract

A tandem carbonyl reduction and hydrodefluorination of β-trifluoromethyl enones with hydrosilanes under transition-metal-free conditions was developed for the synthesis of a variety of valuable gem-difluorovinyl alcohols. The hydrosilane could act as both a reductive agent and a C(sp3)-F bond-breaking promoter under mild reaction conditions. Synthetically useful organofluorides, such as gem-fluorophosphine alkene, gem-difluorovinyl ketone, and fluorinated dihydrofuran derivatives could be readily constructed by further transformations of the obtained gem-difluorovinyl alcohols. Moreover, the method features mild reaction conditions, operational simplicity, excellent functional group tolerance, and scalability.

Original languageEnglish
Article numbere202400274
JournalEuropean Journal of Organic Chemistry
Volume27
Issue number23
DOIs
StatePublished - 17 Jun 2024

Keywords

  • Hydrodefluorination
  • Hydrosilane
  • Transition-metal-free
  • Trifluoromethyl enone
  • gem-Difluoroalkene

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