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Copper-Catalyzed Radical Reaction of N-Tosylhydrazones: Stereoselective Synthesis of (E)-Vinyl Sulfones

Shuai Mao, Ya-Ru Gao, Xue-Qing Zhu, Dong-Dong Guo and Yong-Qiang Wang*

*Key Laboratory of Synthetic and Natural Functional Molecule Chemistry of Ministry of Education, Department of Chemistry & Materials Science, Northwest University, Xi'an 710069, P.R. China, Email: wangyqnwu.edu.cn

S. Mao, Y.-R. Gao, X.-Q. Zhu, D.-D. Guo, Y.-Q. Wang, Org. Lett., 2015, 17, 1692-1695.

DOI: 10.1021/acs.orglett.5b00461 (free Supporting Information)


Abstract

A convenient copper-catalyzed radical reaction of readily available N-tosylhydrazones provides vinyl sulfones with excellent E stereoselectivity and broad substrate scope. An efficient one-pot synthesis of alkynes from N-tosylhydrazones has also been achieved.

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Key Words

vinyl sulfones, alkynes, terminal alkynes


ID: J54-Y2015