Open AccessFluorine-Retentive Strategies for the Functionalization of gem-Difluoroalkenes
Author(s) -
Jacob P. Sorrentino,
Ryan A. Altman
Publication year - 2021
Publication title -
synthesis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.885
H-Index - 140
eISSN - 1437-210X
pISSN - 0039-7881
DOI - 10.1055/a-1547-9270
Subject(s) - chemistry , electrophile , surface modification , fluorine , nucleophile , trifluoromethyl , reactive intermediate , combinatorial chemistry , catalysis , organic chemistry , photochemistry , alkyl
gem -Difluoroalkenes are readily available fluorinated building blocks, and the fluorine-induced electronic perturbations of the alkenes enables a wide array of selective functionalization reactions. However, many reactions of gem -difluoroalkenes result in a net C─F functionalization to generate monofluorovinyl products or addition of F to generate trifluoromethyl-containing products. In contrast, fluorine-retentive strategies for the functionalization of gem -difluoroalkenes remain less generally developed, and is now becoming a rapidly developing area. This review will present the development of fluorine-retentive strategies including electrophilic, nucleophilic, radical, and transition metal catalytic strategies with an emphasis on key physical organic and mechanistic aspects that enable reactivities.