The direct alkylation of unactivated sp3 C鈥揌 bonds of aliphatic amides was achieved via nickel catalysis with the assist of a bidentate directing group. The reaction favors the C鈥揌 bonds of methyl groups over the methylene C鈥揌 bonds and tolerates various functional groups. Moreover, this reaction shows a predominant preference for sp3 C鈥揌 bonds of methyl groups via a five-membered ring intermediate over the sp2 C鈥揌 bonds of arenes in the cyclometalation step.