Cross Coupling of Acyl and Aminyl Radicals: Direct Synthesis of Amides Catalyzed by Bu4NI with TBHP as an Oxidant

被引:390
作者
Liu, Zhaojun [1 ]
Zhang, Jie [1 ]
Chen, Shulin [1 ]
Shi, Erbo [1 ]
Xu, Yuan [1 ]
Wan, Xiaobing [1 ,2 ]
机构
[1] Soochow Univ, Coll Chem Chem Engn & Mat Sci, Key Lab Organ Synth Jiangsu Prov, Suzhou 215123, Peoples R China
[2] Lanzhou Univ, State Key Lab Appl Organ Chem, Lanzhou 730000, Peoples R China
关键词
aldehydes; amides; cross-coupling; formamides; radical reactions; TERT-BUTYL HYDROPEROXIDE; MONOXIDE-FREE AMINOCARBONYLATION; C-H ACTIVATION; CARBOXYLIC-ACIDS; ARYL HALIDES; ONE-POT; INTERMOLECULAR HYDROACYLATION; CARBON-MONOXIDE; METAL-FREE; TRANSFER HYDROAMINATION;
D O I
10.1002/anie.201108763
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A radical solution: A Bu 4NI/tert-butyl hydroperoxide (TBHP) catalyzed synthesis of amides through a cross-coupling reaction between acyl and aminyl radicals is described. This method involves the combination of aldehyde C-H bond functionalization and decarbonylation of N,N-disubstituted formamides (see scheme). The cross-coupling is metal-free, has a wide substrate scope, operational simplicity, and gives high yields on scale-up. Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码:3231 / 3235
页数:5
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