Carbofluorination of π‐Bonds and Related Reactions Involving Tandem C−C/C−F Bond Formation

A review on the carbofluorination of π-bonds and related transformations involving tandem C−C/C−F bond forming reactions is presented. The application of electrophilic fluorine and nucleophilic fluoride reagents in this chemistry is described, as well as recently developed protocols involving the use of fluorinated organic molecules in atom-economic carbofluorination reactions.

Abstract

Due to the unique properties of C−F bonds, organofluorine compounds occupy a privileged space in the pharmaceutical, agrochemical, and polymer industries. Carbofluorination reactions involve the formation of a C−C and a C−F bond, typically across a π-bond or another unsaturated functionality that is revealed upon in situ activation. The design of tailored substrates and new catalyst systems has enabled carbofluorination chemistry to emerge as a promising manifold for the synthesis of unique fluorinated scaffolds. This review covers the application of nucleophilic and electrophilic fluorinating reagents in this chemistry, in addition to recently developed atom-economical carbofluorination reactions using organofluorine compounds as dual reagents.

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