Nickel-catalyzed one-pot C-H alkylation of (hetero)arenes enabled by in situ electrophilic iodination and reductive coupling with alkyl pyridinium salts.

Herein, we report a practical one-pot protocol for the formal C(sp2)-H alkylation of (hetero)arenes by combining in situ I2/Selectfluor-mediated electrophilic iodination with nickel-catalysed reductive cross-coupling using readily accessible alkyl pyridinium salts. The transformation exhibits a broad arene scope and tolerates various functional groups and a range of heterocycles. Importantly, late-stage functionalization of complex bioactive molecules, including dapagliflozin, aniracetam, clofibrate and fenofibrate derivatives, is demonstrated. This method utilized two abundant chemical feedstocks for forging C(sp2)-C(sp3) bonds, offering a versatile and operationally simple entry to alkylarenes.