Iron Catalyzed Oxidative C(sp3)-N Cross Coupling of Amides with C(sp3)-H via a Radical Process

An efficient iron-catalyzed oxidative N-H alkylation of amides with C(sp(3))-H in cycloalkanes, methylarenes and tert-Butyl peroxybenzoate was developed. This protocol proceeded smoothly without any ligand; and tolerated a broad range of substrates, not only various amides but also the inactive C(sp(3))-H bond containing compounds. Mechanistic details involving a Fe(II)/Fe(III) catalytic cycle and a single electron transfer (SET)-type process were also described.