Deuteriodifluoromethylation and  gem ‐Difluoroalkenylation of Aldehydes Using ClCF 2 H in Continuous Flow | Zendy

Fu Wai Chung | Zendy; Jamison Timothy F. | Zendy

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Deuteriodifluoromethylation and gem ‐Difluoroalkenylation of Aldehydes Using ClCF 2 H in Continuous Flow

Author(s) -

Fu Wai Chung,

Jamison Timothy F.

Publication year - 2020

Publication title -

angewandte chemie

Language(s) - English

Resource type - Journals

eISSN - 1521-3757

pISSN - 0044-8249

DOI - 10.1002/ange.202004260

Subject(s) - cycloaddition , chemistry , reagent , unavailability , continuous flow , hydrolysis , deuterium , flow chemistry , functional group , nitrile , organic chemistry , medicinal chemistry , combinatorial chemistry , catalysis , polymer , physics , quantum mechanics , mechanics , engineering , reliability engineering

The deuteriodifluoromethyl group (CF 2 D) represents a challenging functional group due to difficult deuterium incorporation and unavailability of precursor reagents. Herein, we report the use of chlorodifluoromethane (ClCF 2 H) 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 D 2 O to provide α‐deuteriodifluoromethylated benzyl alcohols or undergo a retro [2+2] cycloaddition under thermal conditions to provide the gem ‐difluoroalkenylated product.

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