In summary, we have demonstrated a general copper catalysis system that is uniquely effective in being able to facilitate the asymmetric multicomponent arylative radical cross-couplings of vinylarenes and 1,3-enynes, with oxime carbonates and (hetero)aryl boronic acids. The key to the success of these cross-coupling reactions lies in ready regulation of the redox potential of copper catalysts by combination of visible light activation or/and ligand-ligation, thus enabling better rate match of each step. The mild and redox-neutral catalytic systems permit a broad substrate scope and good functional group toleration, providing practical and versatile access to various enantioenriched high-value chiral 1,1-diarylalkanes, benzylic alkynes, and allenes. We believe the new asymmetric multicomponent cross-coupling reactions will provide a new vista for the use of other types of radicals and boronic acids in the development of related asymmetric radical cross-coupling reactions.