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Published on: May 21, 2019
BrCF2CN for photocatalytic cyanodifluoromethylation
Xin-Jun Yang1, Jin-Hong Lin2,3, Ji-Chang Xiao4
1Key Laboratory of Fluorine and Nitrogen Chemistry and Advanced Materials, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 200032, Shanghai, China.
Abstract:
Considering the unique electronic properties of the CF2 and the CN groups, the CF2CN group has significant potential in drug and agrochemical development, as well as material sciences. However, incorporating a CF2CN group remains a considerable challenge. In this work, we disclose a use of bromodifluoroacetonitrile (BrCF2CN), a cost-effective and readily available reagent, as a radical source for cyanodifluoromethylation of alkyl alkenes, aryl alkenes, alkynes, and (hetero)arenes under photocatalytic conditions. This protocol demonstrates an exceptionally broad substrate scope and remarkable tolerance to various functional groups. Notably, the cyanodifluoromethylation of alkynes predominantly provides sterically hindered alkenes, a thermodynamically unfavorable outcome, and (hetero)arene C-H bonds are directly amenable to cyanodifluoromethylation without pre-functionalization.
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