Elemental sulfur as a sulfuration agent in the copper-catalyzed C-H bond thiolation of electron-deficient arenes

Haiming Yan; Zhiliang Huang; Meng Chen; Cuiting Li; Ya Chen; Meng Gao; Aiwen Lei

doi:10.1039/c7ob02036h

Elemental sulfur as a sulfuration agent in the copper-catalyzed C-H bond thiolation of electron-deficient arenes

Org Biomol Chem. 2017 Oct 11;15(39):8276-8279. doi: 10.1039/c7ob02036h.

Authors

Haiming Yan¹, Zhiliang Huang, Meng Chen, Cuiting Li, Ya Chen, Meng Gao, Aiwen Lei

Affiliation

¹ National Research Center for Carbohydrate Synthesis, Jiangxi Normal University, Nanchang 330022, People's Republic of China. drmenggao@163.com aiwenlei@whu.edu.cn.

PMID: 28937700
DOI: 10.1039/c7ob02036h

Abstract

By utilizing elemental sulfur as the thiolation agent and oxidant, a copper-catalyzed direct C-H bond thiolation of electron-deficient arenes was demonstrated. Various electron-deficient arenes were proved to be suitable for this transformation. Preliminary mechanistic studies indicated that this reaction underwent a radical pathway, in which the trisulfur radical anion (S₃˙^-) might play a vital role. Meanwhile, KIE experiments suggested that C-H bond cleavage was not involved in the rate-determining step.