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

Guoling Huang, Jian Li, Jianrong Li, Jiaming Li, Minghua Sun, Peng Zhou, Lu Chen, Yubing Huang, Shaohua Jiang* and Yibiao Li*

*School of Biotechnology and Health Sciences, Wuyi University, Jiangmen, Guangdong Province 529090, China, Email: wyuchemjsh126.com, Leeyib268126.com

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.

DOI: 10.1021/acs.joc.0c01733

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Abstract

In an environmentally sustainable strategy for the chemoselective heterocyclization of bromoenynes through a sulfuration/cyclization process, inexpensive and safe EtOCS₂K is used as a thiol surrogate and tetrabutylphosphonium bromide and H₂O as a mixed solvent. This transition-metal-free reaction provides a range of substituted thiophenes in good yields.

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Synthesis of Substituted Thiophenes through Dehydration and Heterocyclization of Alkynols

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.

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Key Words

thiophenes, green chemistry

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ID: J42-Y2020