Ru/Ni Dual Catalytic Desulfinative Photoredox Csp2–Csp3 Cross‑Coupling of Alkyl Sulfinate Salts and Aryl Halides

A mild Ru/Ni dual catalytic desulfinative photoredox Csp2–Csp3 cross-coupling reaction of alkyl sulfinate salts with aryl halides has been developed. The optimized catalyst system, consisting of Ru­(bpy)3Cl2, Ni­(COD)2, and DBU, smoothly mediates the coupling of a diverse set of secondary and primary nonactivated alkyl sulfinate salts with a broad range of electron-deficient aryl bromides, electron-rich aryl iodides, and heteroaryl bromides under irradiation with blue light. The procedure is ideal for late-stage introduction of alkyl groups on pharmaceutical intermediates, and the Csp2–Csp3 cross-coupling reaction allowed the rapid synthesis of caseine kinase 1δ inhibitor analogues via a parallel medicinal chemistry effort.