B(C6F5)3-Catalyzed Electron Donor-Acceptor Complex-Mediated Aerobic Sulfenylation of Indoles under Visible-Light Conditions

Wenkai Yuan; Jie Huang; Xin Xu; Long Wang; Xiang-Ying Tang

doi:10.1021/acs.orglett.1c02553

B(C₆F₅)₃-Catalyzed Electron Donor-Acceptor Complex-Mediated Aerobic Sulfenylation of Indoles under Visible-Light Conditions

Org Lett. 2021 Sep 17;23(18):7139-7143. doi: 10.1021/acs.orglett.1c02553. Epub 2021 Aug 27.

Authors

Wenkai Yuan¹, Jie Huang¹, Xin Xu¹, Long Wang¹, Xiang-Ying Tang^{1

2}

Affiliations

¹ School of Chemistry and Chemical Engineering, Huazhong University of Science and Technology, Wuhan, Hubei430074, China.
² Hubei Key Laboratory of Bioinorganic Chemistry and Materia Medica, Huazhong University of Science and Technology, Wuhan, Hubei 430074, China.

PMID: 34449237
DOI: 10.1021/acs.orglett.1c02553

Abstract

An efficient B(C₆F₅)₃-catalyzed aerobic oxidative C-S cross-coupling reaction of thiophenol with indoles was developed, affording a wide range of diaryl sulfides in good yields. An electron donor-acceptor complex between B(C₆F₅)₃ and indoles was formed, facilitating the photoinduced single-electron transfer (SET) from indole substrates to the B(C₆F₅)₃ catalyst. This protocol demonstrates a new reaction model using B(C₆F₅)₃ as a single-electron oxidant.