Direct Transformation of Methyl Imines to -Iminonitriles under Mild and Transition-Metal-Free Conditions

被引：29

作者：

Chen, Feng ^{[1
]}

Huang, Xiaoqiang ^{[1
]}

Cui, Yuxin ^{[1
]}

Jiao, Ning ^{[1
,2
]}

机构：

[1] Peking Univ, State Key Lab Nat & Biomimet Drugs, Sch Pharmaceut Sci, Beijing 100191, Peoples R China

[2] Chinese Acad Sci, State Key Lab Drug Res, Shanghai Inst Mat Med, Shanghai 201203, Peoples R China

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2013年 / 19卷 / 34期

基金：

美国国家科学基金会;

关键词：

CH activation; nitriles; radical reactions; rearrangement; transition-metal free; C-H AMINATION; TRIISOPROPYLSILYL ENOL ETHERS; ALPHA-IMINONITRILES; IMIDOYL CYANIDES; SCHMIDT REACTION; ENAMINE CATALYSIS; ORGANIC-SYNTHESIS; BOND FUNCTIONALIZATION; TRIMETHYLSILYL AZIDE; CONVENIENT SYNTHESIS;

D O I：

10.1002/chem.201301933

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A novel transformation of methyl imines into α-iminonitriles under mild and transition-metal-free conditions is described. Three C sp 3-H bonds are cleaved in a radical pathway at room temperature under air. Simple bromide salts are employed to assist this radical process (see scheme; FG=functional group, PIDA = iodobenzene diacetate, TMS = trimethylsilyl). Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：11199 / 11202

页数：4

共 92 条

[1] Intramolecular [4+2] cycloadditions of iminoacetonitriles: A new class of azadienophiles for hetero Diels-Alder reactions [J].