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Photocatalyzed Cyanodifluoromethylation of Alkenes
Author(s) -
Zhang Min,
Lin JinHong,
Xiao JiChang
Publication year - 2019
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201900466
Subject(s) - cyanation , reagent , chemistry , cyanide , molecule , combinatorial chemistry , carbon fibers , organic chemistry , catalysis , materials science , composite number , composite material
Difluoromethylation is a straightforward and widely applied strategy used to incorporate HCF 2 into organic molecules. In contrast, cyanation reagents are typically volatile or highly toxic, or they require harsh reaction conditions. Incorporation of both CN and HCF 2 into organic molecules, such as alkenes, is a worthwhile but challenging task. A method for photocatalyzed cyanodifluoromethylation of alkenes has been developed, which employs a Ph 3 P + CF 2 CO 2 − /NaNH 2 (or NH 3 ) reagent system. Ph 3 P + CF 2 CO 2 − functions as both the HCF 2 and CN carbon source. A cyanide anion is generated in situ under mild conditions, thereby avoiding the use of toxic cyanation reagents. The photocatalytic method permits cyanodifluoromethylation of a range of alkenes under mild room temperature conditions. The CN group within the products may be further derivatized by standard methods.