Generation of copper fluoroalkyl complexes (CuRFLn) from chlorotrifluoroethylene and −RF transfer to aroyl chlorides

Abstract

Given the importance of fluorinated drugs and agrochemicals, fluoroalkylation of organic electrophiles that can be performed at a late stage of chemical synthesis has attracted a flurry of contributions. New fluoroalkyl groups can be obtained by insertion of fluoroalkenes into Cu–H bonds. Chlorotrifluoroethylene undergoes regioselective insertion in its reaction with Stryker's reagent, [CuH(PPh3)]6 and triphos to give [Cu(CFClCF2H)(μ−κ1,κ2-triphos)]2, which mediates the fluoroalkylation of several aroyl chlorides (triphos = bis(2-diphenylphosphinoethyl)-phenylphosphine). In contrast, attempted −RF transfer to aryl iodides instead affords aryl–aryl coupling products.