Copper‐Catalyzed Oxidative Reaction of β‐Keto Sulfones with Alcohols via C−S Bond Cleavage: Reaction Development and Mechanism Study |
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| Authors: | Yang Wang Zhenghang Qi Jiaqi Tian Dr Jie Zhou Xiaochen Wang Prof?Dr Jianlin Han Prof?Dr Jing Ma Prof?Dr Yi Pan |
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| Institution: | 1. School of Chemistry and Chemical Engineering, State Key Laboratory of Coordination Chemistry, Nanjing University, Nanjing, P. R. China;2. School of Chemistry and Chemical Engineering, Institute of Theoretical and Computational Chemistry, Nanjing University, Nanjing, P. R. China;3. Shenzhen Research Institute of Nanjing University, Shenzhen, China |
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| Abstract: | 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 CuII 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. |
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| Keywords: | aerobic oxidation C– S bond cleavage copper density fuctional calculations β -keto sulfones |
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