In summary, we have developed an unprecedented nickel-catalyzed enantioselective, modular, unified coupling of indole-based N-alkyl-Ni fragments with C(sp 2 )/C(sp) bromides. By the use of easily accessible and stable indole-derived alkenes as nucleophiles, this protocol enables streamlined preparation of enantioenriched N-alkylindole molecules under mild conditions, with previously inaccessible functional group tolerance and chemical space. Application in late-stage diversification of several complex drug molecules and natural products as well as chiral syntheses demonstrates its potential utility in the synthesis of valuable chiral N-alkylated bioactive compounds.