Issue 9, 2023

Metal-free sulfonylation of quinoxalinones to access 2-sulfonyl-oxylated quinoxalines via oxidative O–S cross coupling

Abstract

The C2 sulfonylation of quinoxalinones via a metal-free oxidative S–O cross-coupling strategy for synthesizing 2-sulfonyloxylated quinoxalines is established. It effectively solved the long-standing problems in the C2 transformation of quinoxalinones via a metal-free oxidative O–S coupling strategy. Compared with the traditional C2 transformed quinoxalinones—C2 chlorination method, this protocol is mild, facile, and environmentally friendly and exhibits good atomic economy and excellent functional group tolerance. Moreover, the utility of this methodology and the sulfonyloxyl handles was demonstrated through the synthesis of 2-substituted quinoxaline-based bioactive molecules.

Graphical abstract: Metal-free sulfonylation of quinoxalinones to access 2-sulfonyl-oxylated quinoxalines via oxidative O–S cross coupling

Supplementary files

Article information

Article type
Paper
Submitted
23 Dec 2022
Accepted
30 Jan 2023
First published
09 Feb 2023

Org. Biomol. Chem., 2023,21, 1903-1909

Metal-free sulfonylation of quinoxalinones to access 2-sulfonyl-oxylated quinoxalines via oxidative O–S cross coupling

S. Shi, Y. Yao, J. He, H. Li, S. Han, L. Zhang and Y. Zhao, Org. Biomol. Chem., 2023, 21, 1903 DOI: 10.1039/D2OB02304K

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