Journal of the American Chemical Society, Vol.135, No.16, 6030-6032, 2013
beta-Arylation of Carboxamides via Iron-Catalyzed C(sp(3))-H Bond Activation
A 2,2-disubstituted propionamide bearing an 8-aminoquinolinyl group as the amide moiety can be arylated at the beta-methyl position with an organozinc reagent in the presence of an organic oxidant, a catalytic amount of an iron salt, and a biphosphine ligand at 50 degrees C. Various features of selectivity and reactivity suggest the formation of an organometallic intermediate via rate-determining C-H bond cleavage rather than a free-radical-type reaction pathway.