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

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)(mu-kappa 1,kappa 2-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.

Automated summary

Given the importance of fluorinated drugs and agrochemicals, researchers have been focusing on fluoroalkylation methods that can be performed at a late stage of chemical synthesis. One such method involves the insertion of fluoroalkenes into Cu-H bonds to obtain new fluoroalkyl groups. However, attempts to transfer -RF groups to aryl iodides result in aryl-aryl coupling products instead.