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Amide Synthesis by Nucleophilic Attack of Vinyl Azides
Author(s) -
Zhang FengLian,
Wang YiFeng,
Lonca Geoffroy Hervé,
Zhu Xu,
Chiba Shunsuke
Publication year - 2014
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.201400938
Subject(s) - nucleophile , amide , chemistry , substituent , electrophile , carbocation , azide , enamine , hydrolysis , nucleophilic addition , polymer chemistry , organic chemistry , catalysis
Abstract A method for the synthesis of amide‐containing molecules was developed using vinyl azides as an enamine‐type nucleophile towards carbon electrophiles, such as imines, aldehydes, and carbocations that were generated from alcohols in the presence of BF 3 ⋅OEt 2 . After nucleophilic attack of the vinyl azide, a substituent of the resulting iminodiazonium ion intermediate migrates to form a nitrilium ion, which is hydrolyzed to afford the corresponding amide.

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