Selective functionalization of remote C-H bonds via metal/hydride shift and cross-coupling represents a powerful strategy in modern synthetic chemistry. Herein, we report a highly efficient aryl-to-vinyl 1,4-nickel migration coupled with a reductive cross-coupling for the stereoselective synthesis of conjugated dienes. This tandem process proceeds under mild conditions, accommodates a wide range of substrates, and achieves excellent regioselectivity and Z/E stereoselectivity, offering a valuable method for constructing multisubstituted conjugated dienes.