As a continuation of our interest in the catalytic synthesis of chiral alkylamine-bearing molecules, we report herein the first NiH-catalyzed enantioselective hydrocarbonation of Nindolyl-substituted alkenes with aryl/alkenyl/alkynyl bromides, analogous to the C(sp 3 )-C(sp 2 )/C(sp) cross-coupling reaction, enabling a unified method toward structually diverse chiral N-alkylindoles in high yields and ee's (Fig. ). It is worth noticing that the arene substrates in NiH-catalyzed hydroarylation reactions have commonly been limited to aryl iodides, and use of aryl bromides remained elusive. From a practicality perspective, aryl bromides are usually cheaper, more accessible, and more stable than the corresponding aryl iodides. By employing mild conditions, this modular, unified fragment coupling provides practical advantages in reaction efficiency, functional group compatibility, as well as substrate availability and scope, which would be broadly useful yet mechanistically orthogonal to established N-alkylation processes. In particular, application in late-stage diversifcation of many natural products and drug molecules demonstrates its utility in accelerating access to N-alkylated drug-like complexity.