Transition metal catalyzed cross-coupling is a versatile tool for the construction of (hetero)biaryl scaffolds. However, the crosselectrophile coupling using abundant (hetero)aryl halides and pseudohalides is still in its infancy. In particular, a robust and general method for the cross-electrophile coupling would allow unparalleled entry into the vast collection of commercially available, structurallydiverse (hetero)aryl halides and pseudohalides as coupling partners. We demonstrate herein a ligand controlled visible light driven monometallic cross-electrophile coupling platform in which the synergistic operation of dual palladium catalytic cycle differentiates the electrophiles based on the bond dissociation enthalpy. This method is mild, robust, selective, and displays unique efficacy towards a wide range of functional groups and challenging heteroaryls, providing access to structurally diverse (hetero)biaryl scaffolds. The power of the transformation has been revealed through the synthesis of (hetero)biaryl core of various pharmaceuticals, and diversification of peptides. The synthesis of more than 54% new (hetero)biaryl core has been demonstrated, allowing access to an expanded chemical space for further exploration in functional materials, drug discovery, and bioconjugation-based therapeutics development. Bypassing the traditional transmetalation step, this technology enables a general strategy for the cross-electrophile coupling of (hetero)aryl halides and pseudohalides.