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Cross Coupling of Acyl and Aminyl Radicals: Direct Synthesis of Amides Catalyzed by Bu 4 NI with TBHP as an Oxidant
Author(s) -
Liu Zhaojun,
Zhang Jie,
Chen Shulin,
Shi Erbo,
Xu Yuan,
Wan Xiaobing
Publication year - 2012
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201108763
Subject(s) - decarbonylation , radical , aldehyde , catalysis , chemistry , formamides , substrate (aquarium) , scope (computer science) , coupling (piping) , combinatorial chemistry , organic synthesis , organic chemistry , computer science , materials science , oceanography , metallurgy , programming language , geology
A radical solution : A Bu 4 NI/ 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 CH 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.