A visible-light-induced thiol addition/aerobic oxidation cascade reaction of epoxides and thiols for the synthesis of β-hydroxylsulfoxides

Abstract

A photochemical thiol addition/aerobic oxidation cascade reaction has been developed. This protocol enables efficient oxidative coupling of epoxides and thiols to access structurally valuable β-hydroxylsulfoxides. A broad range of functional groups are compatible to obtain moderate to good yields of the target products. Mechanistic studies revealed a sequential reaction pathway involving base-promoted thiol addition of thiols to epoxides and visible-light-induced aerobic oxygenation of thioethers.