Nickela‐electrocatalyzed Mild C−H Alkylations at Room Temperature

Direct alkylations of carboxylic acid derivatives are challenging and particularly nickel catalysis commonly requires high reaction temperatures and strong bases, translating into limited substrate scope. Herein, nickel‐catalyzed C−H alkylations of unactivated 8‐aminoquinoline amides have been realized under exceedingly mild conditions, namely at room temperature, with a mild base and a user‐friendly electrochemical setup. This electrocatalyzed C−H alkylation displays high functional group tolerance and is applicable to both the primary and secondary alkylation. Based on detailed mechanistic studies, a nickel(II/III/I) catalytic manifold has been proposed. Electrochemically enabled nickel‐catalyzed C−H alkylations with primary and secondary alkyl halides have been accomplished under exceedingly mild reaction conditions with Et3N at room temperature. Detailed mechanistic studies provided support for a nickel(II/III/I) manifold.