Nickel-catalyzed oxidative dehydrogenative coupling of alkane with thiol for C(sp3)-S bond formation

Abstract A nickel-catalyzed oxidative dehydrogenative coupling reaction of alkane with thiol for the construction of C(sp3)-S bond has been established, affording more than 50 alkyl thioethers. Notably, pharmaceutical and agrochemicals, such as Provigil, Chlorbenside and Pyridaben, were readily synthesized by this approach. The sterically hindered ligand BC and disulfide which was formed in situ oxidation of thiol, efficiently avoiding nickel-catalyst poisoning. A set of mechanistic experiments disclose both Ni-catalyzed and Ni-free HAA processes.