A total of 19 alkylated heterocycles (thiophenes, benzothiophenes, pyrroles, furans) were prepared (36–99% yield) from the respective pyridin-2-yl-substituted precursors employing alkylboronic acids as the C–H alkylating reagents in an oxidative (Ag₂CO₃ and 2,6-dimethyl-1,4-benzoquinone as oxidants) Pd-catalysed coupling reaction.