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

Author:

Li Linwei1,Zhou Yi2,Xi Zhenguo1,Guo Zhaoquan1,Duan Ji‐Cheng2,Yu Zhi‐Xiang2,Gao Hongyin1ORCID

Affiliation:

1. School of Chemistry and Chemical Engineering Shandong University 27 South Shanda Road Ji'nan 250100 Shandong China

2. Beijing National Laboratory for Molecular Sciences (BNLMS) Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education College of Chemistry Peking University Beijing 100871 China

Abstract

AbstractA 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‐[2π+2σ] cycloaddition via a stepwise diradical mechanism to form the N−N bond and release SO2.

Funder

National Natural Science Foundation of China

Taishan Scholar Foundation of Shandong Province

Publisher

Wiley

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