A cobalt catalyst, under oxidative conditions, facilitates the single electron transfer process in N-pyridyl arylacetamides to form α-carbon-centered radicals that readily react with molecular oxygen, giving access to mandelic acid derivatives. In contrast to the known benzylic hydroxylation approaches, this approach enables chemo- and regioselective hydroxylation at a benzylic position adjacent to (N-pyridyl)amides. Mild conditions, broad scope, excellent selectivity, and wide synthetic practicality set up the merit of the reaction.