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 language | English |
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Pages (from-to) | 13885-13890 |
Number of pages | 6 |
Journal | Angewandte Chemie - International Edition |
Volume | 59 |
Issue number | 33 |
DOIs | |
Publication status | Published - 10 Aug 2020 |
Externally published | Yes |
Keywords
- chlorodifluoromethane
- continuous flow
- deuteration
- difluoromethylation
- gem-difluoroalkene
ASJC Scopus subject areas
- Catalysis
- Chemistry(all)