Premium
Copper‐Catalyzed Oxidative Reaction of β‐Keto Sulfones with Alcohols via C−S Bond Cleavage: Reaction Development and Mechanism Study
Author(s) -
Du Bingnan,
Wang Wenmin,
Wang Yang,
Qi Zhenghang,
Tian Jiaqi,
Zhou Jie,
Wang Xiaochen,
Han Jianlin,
Ma Jing,
Pan Yi
Publication year - 2018
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201701694
Subject(s) - chemistry , bond cleavage , homolysis , catalysis , oxidative phosphorylation , cleavage (geology) , reaction mechanism , radical , medicinal chemistry , organic chemistry , combinatorial chemistry , biochemistry , geotechnical engineering , fracture (geology) , engineering
A Cu‐catalyzed cascade oxidative radical process of β‐keto sulfones with alcohols has been achieved by using oxygen as an oxidant. In this reaction, β‐keto sulfones were converted into sulfinate esters under the oxidative conditions via cleavage of C−S bond. Experimental and computational studies demonstrate that a new pathway is involved in this reaction, which proceeds through the formation of the key four‐coordinated Cu II intermediate, O−O bond homolysis induced C−S bond cleavage and Cu‐catalyzed esterification to form the final products. This reaction provides a new strategy to sulfonate esters and enriches the research content of C−S bond cleavage and transformations.