Deuteriodifluoromethylation and gem‐Difluoroalkenylation of Aldehydes Using ClCF2H in Continuous Flow
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.
Document Details
- Document Type
- Pub Defense Publication
- Publication Date
- Jun 04, 2020
- Source ID
- 10.1002/ange.202004260
Entities
People
- Timothy F. Jamison
- Wai Chung Fu
Organizations
- Croucher Foundation
- Defense Advanced Research Projects Agency
- Massachusetts Institute of Technology