Photocatalytic Reductive Borylation, Phosphonation, Sulfurization, and Selenization of Aryl Iodides to Access Aryl Borates, Aryl Phosphates, Aryl Sulfides, and Aryl Selenides

A simple photoinduced radical borylation, phosphonation, sulfurization and selenization of various aryl iodides to construct the structurally diverse C-B/P/S/Se bonds has been developed. Using HCO₂Na as the reductant, a wide range of aryl iodides including the substituted iodobenzenes, heteroaromatic iodides, aromatic iodides derived from the pharmaceutically active molecules could be utilized to react with the bis(pinacolato)diboron, triethyl phosphite, (RS)₂ or (RSe)₂ to obtain a variety of aryl borates, aryl phosphates, aryl sulfides and aryl selenides in general moderate to good yields.The advantage of this protocol is also highlighted by its no extra metal/photocatalyst, gram-scale synthesis and the further functional transformations of the products.