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Copper-Catalyzed Sulfenylation, Sulfonylation, and Selenylation of 2,3-Allenoic Acids with Disulfides or Diselenides

Ya-Xun Xin, Shen Pan, Yangen Huang*, Xiu-Hua Xu* and Feng-Ling Qing

*Donghua University, 2999 North Renmin Lu, Shanghai 201620; Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032, China, Email: hygdhu.edu.cn, xuxiuhuasioc.ac.cn

Y.-X. Xin, S. Pan, Y. Huang, X.-H. Xu, F.-L. Qing, J. Org. Chem., 2018, 83, 6101-6109.

DOI: 10.1021/acs.joc.8b00858 (free Supporting Information)


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Abstract

An efficient copper-catalyzed sulfenylation and selenylation of 2,3-allenoic acids with disulfides or diselenides afford various 4-sulfenylated and 4-selenylated butenolides in good yields via tandem radical addition/intramolecular cyclization processes. Moreover, 4-sulfonylated butenolides could also be obtained by sulfenylation of 2,3-allenoic acids and subsequent oxidation.

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Key Words

butenolides, ammonium peroxydisulfate


ID: J42-Y2018