Cu(I)-catalyzed, N-Fluorobenzamides Enabling 1,2-Carbofluorination of Unactivated Alkenes via Free Radical Relay

Abstract

The construction of carbon-fluorine bond has always remained challenging. This work described a two-component 1,2carbofluorination bifunctionalization of unactivated alkenes through a free radical relay process. The N-fluorobenzamide was firstly used as a unique carbofluoro-bifunctional molecule to attack the unactivated alkenes with the concomitant formation of C-C bond and C-F bond. This reaction initially underwent a N-F bond homolysis to give nitrogen free radical, with the subsequent 1,5-H atom transfer to generate the remote benzylic carbon free radical, and further attacked the alkene to render new alkyl free radical, and followed by single electron transfer of active metal copper species, finally, a series of β-fluoroamides was obtained in moderate yields. This reaction also features excellent atom economy without any atom lost, mild reaction conditions and facile operation.