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 language | English |
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Article number | e202400274 |
Journal | European Journal of Organic Chemistry |
Volume | 27 |
Issue number | 23 |
DOIs | |
State | Published - 17 Jun 2024 |
Keywords
- Hydrodefluorination
- Hydrosilane
- Transition-metal-free
- Trifluoromethyl enone
- gem-Difluoroalkene