Efficient Synthesis of Vinyl Sulfones by Manganese-Catalyzed Decarboxylative Coupling of Cinnamic Acids with Aromatic Sulfinic Acid Sodium Salts

Na Xue, Ruqing Guo, Xinman Tu, Weiping Luo, Wei Deng*, Jiannan Xiang*

*College of Chemistry and Chemical Engineering, State Key Laboratory of Chemo/Biosensing and Chemometrics, Hunan University, Changsha 410082, P. R. of China, Email: weidenghnu.edu.cn, jnxianghnu.edu.cn

N. Xue, R. Guo, X. Tu, W. Luo, W. Deng, J. Xiang, Synlett, 2016, 27, 2695-2698.

DOI: 10.1055/s-0035-1562476

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Abstract

Reactions of cinnamic acids with aromatic sulfinic acid sodium salts in the presence of a catalytic amount of manganese(II) acetate tetrahydrate in dimethyl sulfoxide provide vinyl sulfones in very good yields. The use of DMSO as solvent and the presence of air are critical in achieving good yields.

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Key Words

manganese catalysis, oxygen, DMSO, decarboxylation, coupling, cinnamic acids, sodium arenesulfinates, vinyl sulfones

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ID: J60-Y2016