Methylene-Tethered Arylsulfonation and Benzotriazolation of Aryl/Heteroaryl C-H Bonds with DMSO as a One-Carbon Surrogate.

The Selectfluor-mediated approach toward the synthesis of methylene-tethered arylsulfonation and benzotriazolation of imidazopyridines has been described. The reaction involves imidazopyridine, aryl sulfinate, or benzotriazole and dimethyl sulfoxide (DMSO) in the presence of Selectfluor, where DMSO acts as a one-carbon synthon. The protocol has been extended to the methylene-tethered arylsulfonation and benzotriazolation of β-naphthols. The mechanistic insights show that the intermediate 3-((methylthio)methyl)-2-phenylimidazo[1,2-]pyridine is generated from imidazopyridine, DMSO, and Selectfluor. The nucleophilic displacement by the aryl sulfinate salt or benzotriazole on the intermediate afforded the product.