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

共 68 条

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TUNDO, A ;

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[2]

[Anonymous], Deposition numbers 2380345 (for 18) and 2017565 (for 32) contain the supplementary crystallographic data for this paper. These data are provided free of charge by the joint Cambridge Crystallographic Data Centre and Fachinformationszentrum Karlsruhe Access Structures service

[3] Development of a Nickel-Catalyzed N-N Coupling for the Synthesis of Hydrazides [J].