Direct C-H Thiolation for Selective Cross-Coupling of Arenes with Thiophenols via Aerobic Visible-Light Catalysis

Ge Liang; Jing-Hao Wang; Tao Lei; Yuan-Yuan Cheng; Chao Zhou; Ya-Jing Chen; Chen Ye; Bin Chen; Chen-Ho Tung; Li-Zhu Wu

doi:10.1021/acs.orglett.1c03090

Direct C-H Thiolation for Selective Cross-Coupling of Arenes with Thiophenols via Aerobic Visible-Light Catalysis

Org Lett. 2021 Oct 15;23(20):8082-8087. doi: 10.1021/acs.orglett.1c03090. Epub 2021 Oct 5.

Authors

Ge Liang^{1

2}, Jing-Hao Wang^{1

2}, Tao Lei^{1

2}, Yuan-Yuan Cheng^{1

2}, Chao Zhou^{1

2}, Ya-Jing Chen^{1

2}, Chen Ye^{1

2}, Bin Chen^{1

2}, Chen-Ho Tung^{1

2}, Li-Zhu Wu^{1

2}

Affiliations

¹ Key Laboratory of Photochemical Conversion and Optoelectronic Materials, Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Beijing 100190, P. R. China.
² School of Future Technology, University of Chinese Academy of Sciences, Beijing 100049, P. R. China.

PMID: 34609892
DOI: 10.1021/acs.orglett.1c03090

Abstract

An aerobic metal-free, visible-light-induced regioselective thiolation of phenols with thiophenols is reported. The cross-coupling protocol exhibits great functional group tolerance and high regioselectivity. Mechanistic studies reveal that the disulfide radical cation plays a crucial role in the visible-light catalysis of aerobic thiolation. Simply controlling the equivalent ratio of substrates enables the selective formation of sulfide or sulfoxide products with high activity in a one-pot reaction.