Tandem Flavin-Iodine-Catalyzed Aerobic Oxidative Sulfenylation of Imidazo[1,2- a]Pyridines with Thiols.
Hiroki IidaRyuta DemizuRyoma OhkadoPublished in: The Journal of organic chemistry (2018)
A green, aerobic sulfenylation of imidazo[1,2- a]pyridines was performed using thiols, a flavin-and-iodine dual catalytic system, and environmentally benign molecular oxygen as the only sacrificial reagent. The dual metal-free catalysts smoothly promote a unique stepwise tandem process, beginning with the aerobic oxidation of a thiol to afford a disulfide that is utilized in the oxidative sulfenylation of the imidazo[1,2- a]pyridine. This process has afforded diverse 3-sulfenylimidazo[1,2- a]pyridines of biological interest and is environmentally friendly, as benign H2O is the only byproduct.