Electrochemical Reductive Smiles Rearrangement for C-N Bond Formation

被引：33

作者：

Chang, Xihao ^{[1
]}

Zhang, Qinglin ^{[1
]}

Guo, Chang ^{[1
]}

机构：

[1] Univ Sci & Technol China, Hefei Natl Lab Phys Sci Microscale, Hefei 230026, Anhui, Peoples R China

来源：

ORGANIC LETTERS | 2019年 / 21卷 / 01期

基金：

中国国家自然科学基金;

关键词：

H FUNCTIONALIZATION; OXIDATIVE AMINATION; ELECTRON-TRANSFER; AMIDYL RADICALS; METAL; GENERATION; CLEAVAGE; ETHERS; ELECTROSYNTHESIS; HETEROARENES;

D O I：

10.1021/acs.orglett.8b03178

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A conceptually new and synthetically valuable radical Smiles rearrangement reaction is reported under undivided electrolytic conditions. This protocol employs an entirely new strategy for the electrochemical radical Smiles rearrangement. Remarkably, an amidyl radical generated from the cleavage of the N-O bond under reductive electrolytic conditions plays a crucial role in this transformation. Various hydroxylamine derivatives bearing different substituents are suitable in this electrochemical transformation, furnishing the corresponding amides in up to 86% yield.

引用

页码：10 / 13

页数：4

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