Photochemical Organocatalytic Aerobic Cleavage of C═C Bonds Enabled by Charge-Transfer Complex Formation

Abstract

A novel visible-light-driven organocatalytic protocol to access aerobic oxidative cleavage of olefins, promoted by sodium benzene sulfinate, is described herein. An array of alkenes smoothly delivered the corresponding aldehydes and ketones under transition-metal-free conditions. Notably, α-halo-substituted styrenes proceeded with photoinduced oxidation to finally afford α-halo-acetophenones with halogen migration. Crucial to this oxidation was the formation of charge-transfer complexes between sodium benzene sulfinate with molecular O₂ to ultimately deliver the carbonyl products.