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Copper-Catalyzed Aerobic Decarboxylative Sulfonylation of Cinnamic Acids with Sodium Sulfinates: Stereospecific Synthesis of (E)-Alkenyl Sulfones

Qing Jiang, Bin Xu, Jing Jia, An Zhao, Yu-Rou Zhao, Ying-Ying Li, Na-Na He and Can-Cheng Guo*

*Advanced Catalytic Engineering Research Center of the Ministry of Education, College of Chemistry and Chemical Engineering, Hunan University, Changsha, China, Email: ccguohnu.edu.cn

Q. Jiang, B. Xu, J. Jia, A. Zhao, Y.-R. Zhao, Y.-Y. Li, N.-N. He, C.-C. Guo, J. Org. Chem., 2014, 79, 7372-7379.

DOI: 10.1021/jo5010845 (free Supporting Information)


Abstract

A copper-catalyzed aerobic decarboxylative sulfonylation of alkenyl carboxylic acids with sodium sulfinates offers an expedient strategy for stereoselective synthesis of (E)-alkenyl sulfones that are widely present in biologically active natural products and therapeutic agents. The transformation proceeds via a radical process and exhibits a broad substrate scope and good functional group tolerance.

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Key Words

Vinyl sulfones, Oxygen


ID: J42-Y2014