Thiol-initiated photocatalytic oxidative cleavage of the CC bond in olefins and its extension to direct production of acetals from olefins

Abstract

The oxidative cleavage of olefins to produce aldehydes/ketones is an important reaction in organic syntheses. In this manuscript, a mild and operationally simple protocol for the aerobic oxidation of olefins to produce carbonyl compounds was realized over ZnIn₂S₄ under visible light, using air as the oxidant and a thiol as the initiator. It was proposed that the photogenerated holes over ZnIn₂S₄ attack the thiol to produce thiyl radicals, which initiate the oxidative cleavage of the CC bond in olefins to produce aldehydes/ketones. By further coupling with the condensation between the as-obtained aldehydes/ketones and alcohols, this strategy can also be applied to the production of different acetals directly from the olefins. This study demonstrates a new pathway to realize the oxidative cleavage of olefins to produce aldehydes/ketones, and also provides a new protocol for the production of acetals directly from the olefins.