Desulfurdioxidative N-N Coupling of N-Arylhydroxylamines and N-Sulfinylanilines: Reaction Development and Mechanism

被引：2

作者：

Li, Linwei ^{[1
]}

Zhou, Yi ^{[2
]}

Xi, Zhenguo ^{[1
]}

Guo, Zhaoquan ^{[1
]}

Duan, Ji-Cheng ^{[2
]}

Yu, Zhi-Xiang ^{[2
]}

Gao, Hongyin ^{[1
]}

机构：

[1] Shandong Univ, Sch Chem & Chem Engn, 27 South Shanda Rd, Jinan 250100, Shandong, Peoples R China

[2] Peking Univ, Coll Chem, Beijing Natl Lab Mol Sci BNLMS, Key Lab Bioorgan Chem & Mol Engn,Minist Educ, Beijing 100871, Peoples R China

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2024年 / 63卷 / 26期

基金：

中国国家自然科学基金;

关键词：

N-arylhydroxylamines; N-sulfinylanilines; N-N coupling; retro-[2 pi+2 sigma] cycloaddition; N; N '-diaryl hydrazines; ARYL HYDRAZINES; OXIDATIVE DEHYDROGENATION; HYDRAZOBENZENES; CYCLOADDITIONS; REDUCTION; HALIDES; BOND; METHYLENECYCLOPROPANE; HYDROGENATION; CATALYSIS;

D O I：

10.1002/anie.202406478

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A highly efficient and chemoselective approach for the divergent assembling of unsymmetrical hydrazines through an unprecedented intermolecular desulfurdioxidative N-N coupling is developed. This metal free protocol employs readily accessible N-arylhydroxylamines and N-sulfinylanilines to provide highly valuable hydrazine products with good reaction yields and excellent functional group tolerance under simple conditions. Computational studies suggest that the in situ generated O-sulfenylated arylhydroxylamine intermediate undergoes a retro-[2 pi+2 sigma] cycloaddition via a stepwise diradical mechanism to form the N-N bond and release SO2.

引用

页数：7

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