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Synfacts 2020; 16(08): 1001
DOI: 10.1055/s-0040-1706897
Flow Chemistry
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Deuterodifluoromethylated Alcohols and gem-Difluoroalkenes in Continuous Flow

Contributor(s):
Paul Knochel
,
Alexander Kremsmair
Fu WC, Jamison TF. * Massachusetts Institute of Technology, Cambridge, USA
Deuteriodifluoromethylation and gem-Difluoroalkenylation of Aldehydes Using ClCF2H in Continuous Flow.

Angew. Chem. Int. Ed. 2020;
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Publication History

Publication Date:
21 July 2020 (online)

 
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Key words

continuous flow - deuteration - difluoromethylation - gem-difluoroalkenes

Significance

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.


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Comment

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.


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