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Synthesis of Substituted Thiophenes through Dehydration and Heterocyclization of Alkynols

Jian Li, Yang Liu, Zebin Chen, Jiaming Li, Xiaoliang Ji, Lu Chen, Yubing Huang, Qiang Liu* and Yibiao Li*

*School of Biotechnology and Health Sciences, Wuyi University, Jiangmen, Guangdong 529090, China, Email: qiang_liumail.tsinghua.edu.cn, leeyib268126.com

J. Li, Y. Liu, Z. Chen, J. Li, j. Li, X. Ji, L. Chen, Y. Huang, Q. Liu, Y. Li, J. Org. Chem., 2022, 87, 3555-3566.

DOI: 10.1021/acs.joc.1c03114


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Abstract

A metal-free dehydration and sulfur cyclization of alkynols with elemental sulfur (S8) or EtOCS2K provides a variety of substituted thiophenes in good yields. The reaction is initiated by the base-free generation of a trisulfur radical anion (S3-) and its addition to alkynes.

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proposed mechanism



Access to Substituted Thiophenes through Xanthate-Mediated Vinyl C(sp2)-Br Bond Cleavage and Heterocyclization of Bromoenynes

G. Huang, J. Li, J. Li, J. Li, M. Sun, P. Zhou, L. Chen, Y. Huang, S. Jiang, Y. Li, J. Org. Chem., 2020, 85, 13037-13049.


Key Words

thiophenes


ID: J42-Y2022