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Transition-Metal-Free Sulfuration/Annulation of Alkenes: Economical Access to Thiophenes Enabled by the Cleavage of Multiple C-H Bonds

Liang Chen, Hao Min, Weilan Zeng, Xiaoming Zhu, Yun Liang*, Guobo Deng*, Yuan Yang*

*Hunan Normal University, Changsha, Hunan 410081, China, Email: ylianghunnu.edu.cn, yangyuan071126.com

L. Chen, H. Min, W. Zeng, X. Zhu, Y. Liang, G. Deng, Y. Yang, Org. Lett., 2018, 20, 7392-7395.

DOI: 10.1021/acs.orglett.8b03078 (free Supporting Information)


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Abstract

The reaction of substituted buta-1-enes with potassium sulfide enables an atom economical, and transition-metal-free synthesis of thiophenes via cleavage of multiple C-H bonds. Moreover, the strategy can also be used for the synthesis of thiophenes from 1,4-diaryl-1,3-dienes.

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proposed mechanism



Key Words

thiophenes, DMSO


ID: J54-Y2018