Issue 24, 2023

Visible-light-induced electron donor–acceptor (EDA) complex-initiated synthesis of non-anomeric S-aryl glycosides

Abstract

A visible-light-induced protocol for the preparation of S-aryl thioglycosides has been reported. This metal- and photocatalyst-free protocol is based on electron donor–acceptor (EDA) complexes formed between glycosyl N-hydroxyphthalimide esters and thiophenol. This method avoids the use of high temperature, transition metals and photocatalysts, providing an environmentally friendly, simple and efficient protocol. This process gives access to a series of S-aryl thioglycosides in moderate to excellent yields with good control of the anomeric configuration.

Graphical abstract: Visible-light-induced electron donor–acceptor (EDA) complex-initiated synthesis of non-anomeric S-aryl glycosides

Supplementary files

Article information

Article type
Research Article
Submitted
14 Sep 2023
Accepted
24 Oct 2023
First published
07 Nov 2023

Org. Chem. Front., 2023,10, 6200-6204

Visible-light-induced electron donor–acceptor (EDA) complex-initiated synthesis of non-anomeric S-aryl glycosides

J. Hou, L. Zhang, S. He, M. Ye, J. Chen, T. Huang, G. Lv, L. Hai, Z. Yang and Y. Wu, Org. Chem. Front., 2023, 10, 6200 DOI: 10.1039/D3QO01495A

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