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Synthesis of Deuterodifluoromethylated Alcohols and gem-Difluoroalkenes in Continuous Flow
Deuteriodifluoromethylation and gem-Difluoroalkenylation of Aldehydes Using ClCF2H in Continuous Flow.
Angew. Chem. Int. Ed. 2020;
21 July 2020 (online)
Fu and Jamison report the utilization of chlorodifluoromethane gas in a continuous-flow setup for the preparation of α-deuteriodifluoromethylated benzyl alcohols and gem-difluoroalkenes from a range of aldehydes in good yields.
Interestingly, the authors performed NMR studies that led them to propose a plausible reaction mechanism involving an oxaphosphetane intermediate. Furthermore, the authors demonstrated the utility of this method by performing various derivatizations of the α-deuteriodifluoromethylated benzyl alcohol, affording the corresponding, bromide, tosylate or ketone.