Amide Synthesis by Nucleophilic Attack of Vinyl Azides1. Issue 17 (18th March 2014)

• Record Type: Journal Article
• Authors: Zhang, Feng‐Lian; Wang, Yi‐Feng; Lonca, Geoffroy Hervé; Zhu, Xu; Chiba, Shunsuke
• Is Part Of: Angewandte Chemie international edition. Volume 53:Issue 17(2014)
• Page Start: 4390
• Page End: 4394
• Publication Date: 2014-03-18
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201400938
• Languages: English
• ISSNs: 1433-7851

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>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.</p> </abstract>