Fe-promoted radical cyanomethylation/arylation of arylacrylamides to access oxindoles via cleavage of the sp(3) C-H of acetonitrile and the sp(2) C-H of the phenyl group.

Radical cyanomethylation/arylation of arylacrylamides to access oxindoles with acetonitrile as the radical precursor is described. This reaction involves dual C-H bond functionalization, including the sp(3) C-H of acetonitrile and the sp(2) C-H of the phenyl group. A variety of functional groups, such as methoxy, ethyloxy carbonyl, chloro, bromo, iodo, nitro, trifluoromethoxy and trifluoromethyl groups, are well tolerated.