Enantioselective C–H amidation of sulfondiimines for the synthesis of 1,2,4-benzothiadiazine-1-imines under cobalt catalysis

Abstract

In comparison to the notable recent progress in the derivatization of sulfoximines via directed C–H activation, the C–H activation/functionalization of sulfondiimines is underdeveloped. Here, we report C–H amidation/cyclization reactions of sulfondiimines with dioxazolones catalyzed by the combination of a cobalt(III) catalyst and a pseudo C2-symmetric chiral carboxylic acid, leading to the formation of unprecedented 1,2,4-benzothiadiazine-1-imine structures in high enantioselectivity.

Graphical abstract: Enantioselective C–H amidation of sulfondiimines for the synthesis of 1,2,4-benzothiadiazine-1-imines under cobalt catalysis

Supplementary files

Article information

Article type
Research Article
Submitted
20 Feb 2025
Accepted
03 Apr 2025
First published
04 Apr 2025
This article is Open Access
Creative Commons BY license

Org. Chem. Front., 2025, Advance Article

Enantioselective C–H amidation of sulfondiimines for the synthesis of 1,2,4-benzothiadiazine-1-imines under cobalt catalysis

A. Murata, T. Endo, Y. Hirata, K. Higashida, T. Yoshino and S. Matsunaga, Org. Chem. Front., 2025, Advance Article , DOI: 10.1039/D5QO00355E

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