The synergistic combination of NiH-catalyzed alkene isomerization with nickel-catalyzed cross-coupling has yielded a general protocol for the synthesis of a wide range of structurally diverse 1,1-diarylalkanes in excellent yields and high regioselectivities from readily accessible olefin starting materials. Furthermore, the practicality and synthetic flexibility of this approach is highlighted by the successful employment of isomeric mixtures of olefins for regioconvergent arylation.