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

IF 4.7 1区 化学 Q1 CHEMISTRY, ORGANIC Organic Chemistry Frontiers Pub Date : 2025-04-04 DOI:10.1039/D5QO00355E
Ayami Murata, Tomonori Endo, Yuki Hirata, Kosuke Higashida, Tatsuhiko Yoshino and Shigeki Matsunaga
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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.

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钴催化合成1,2,4-苯并噻唑二嗪-1-亚胺的对映选择性C-H胺化
与近年来通过C-H活化的亚砜酰亚胺衍生化的显著进展相比,C-H活化/功能化的磺基二亚胺尚不发达。本文报道了在钴(III)催化剂和伪c2对称手性羧酸的催化下,磺胺二亚胺与二恶唑酮的C-H酰胺化/环化反应,形成了前所未有的1,2,4-苯并噻唑二嗪-1-亚胺结构,具有高对映选择性。
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来源期刊
Organic Chemistry Frontiers
Organic Chemistry Frontiers CHEMISTRY, ORGANIC-
CiteScore
7.90
自引率
11.10%
发文量
686
审稿时长
1 months
期刊介绍: Organic Chemistry Frontiers is an esteemed journal that publishes high-quality research across the field of organic chemistry. It places a significant emphasis on studies that contribute substantially to the field by introducing new or significantly improved protocols and methodologies. The journal covers a wide array of topics which include, but are not limited to, organic synthesis, the development of synthetic methodologies, catalysis, natural products, functional organic materials, supramolecular and macromolecular chemistry, as well as physical and computational organic chemistry.
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