Photocatalytic Decarboxylative Fluoroalkylation of α,β-Unsaturated Carboxylic Acids

A decarboxylative fluoroalkylation of α,β-unsaturated acids was developed by the use of a dual nickel/photoredox catalysis system. The fluoroalkyl radicals are generated from α-CF3 alkyl bromides by nickel-induced single electron transfer (SET) and are subsequently intercepted by a cinnamic acid to forge the targeted C-C bonds. A wide variety of substrates bearing a diverse set of functional groups were compatible with the mild reaction conditions (visible light, room temperature, cheap metal, no strong oxidant or reductant), thus affording trifluoromethyl analogues of α-methylated allylic compounds.