Photochemical Organocatalytic Aerobic Cleavage of C═C Bonds Enabled by Charge-Transfer Complex Formation
Yixuan Chen, Jun-Tao He, Mei‐Chun Wu, Zhilin Liu, Kai Tang, Peng‐Ju Xia, Kai Chen, Hao‐Yue Xiang, Xiaoqing Chen, Hua Yang
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.
Topics & Concepts
ChemistryBenzenePhotochemistryCleavage (geology)Oxidative cleavageBond cleavageHalogenCharge-transfer complexCatalysisOrganic chemistryAlkylGeotechnical engineeringFracture (geology)EngineeringRadical Photochemical ReactionsSulfur-Based Synthesis TechniquesOxidative Organic Chemistry Reactions