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 (free Supporting Information)

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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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Key Words

thiophenes, green chemistry

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ID: J42-Y2020