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Title: Amide synthesis by nucleophilic attack of vinyl azides
Authors: Zhang, Feng-Lian
Wang, Yi-Feng
Lonca, Geoffroy Hervé
Zhu, Xu
Chiba, Shunsuke
Keywords: DRNTU::Science::Chemistry::Inorganic chemistry::Synthesis
Issue Date: 2014
Source: Zhang, F.-L., Wang, Y.-F., Lonca, G. H., Zhu, X., & Chiba, S. (2014). Amide Synthesis by Nucleophilic Attack of Vinyl Azides. Angewandte Chemie International Edition, 53(17), 4390-4394.
Series/Report no.: Angewandte chemie international edition
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 BF3⋅OEt2. 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.
ISSN: 1433-7851
DOI: 10.1002/anie.201400938
Rights: © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
Fulltext Permission: none
Fulltext Availability: No Fulltext
Appears in Collections:SPMS Journal Articles

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