Organic Chemistry Portal



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:,

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)

see article for more reactions


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.


see article for more examples

Key Words

thiophenes, green chemistry

ID: J42-Y2020