Photoinduced Deoxygenation Reduction of Sulfoxides with HCl or HBr and Hydrocarbons
Feng Xu1, Zemin Wang2, Dayong Shi2
1The Affiliated Hospital of Qingdao University, Qingdao 266000, China.
Abstract:
The deoxygenative reduction of sulfoxides to thioethers represents one of the most important transformations in organic synthesis, garnering significant attention in both academic research and industrial applications. Herein, we report a photoinduced deoxygenative reduction of sulfoxides using inexpensive hydrocarbon species and HX (X = Cl, Br) as combined reductants, which proceeds under mild conditions without the photocatalysts and metals. Mechanistically, this transformation is enabled by a proton-coupled electron transfer process between the SIV═O group and HX. This protocol exhibits a broad substrate scope, excellent functional group tolerance, and operational simplicity.
Related Concept Videos
Preparation and Reactions of Thiols
Oxidation of Alcohols
The process of oxidation in a chemical reaction is observed in any of the three forms:
Oxidative Cleavage of Alkenes: Ozonolysis
Ozone is a symmetrical bent molecule stabilized by a resonance structure.
Preparation and Reactions of Sulfides
Aldehydes and Ketones to Alkanes: Wolff–Kishner Reduction
Oxidation of Phenols to Quinones
o-hydroxy phenols are oxidized to o-quinones and p-hydroxy phenols to p-quinones. Such redox reactions involve the transfer of two electrons and two protons. The reversible redox...


