title: Amide synthesis by nucleophilic attack of vinyl azides.
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.
authors.affiliation: Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637371 (Singapore).
authors.forename: Feng-Lian
authors.initials: FL
authors.lastname: Zhang
authors.forename: Yi-Feng
authors.initials: YF
authors.lastname: Wang
authors.forename: Geoffroy Hervé
authors.initials: GH
authors.lastname: Lonca
authors.forename: Xu
authors.initials: X
authors.lastname: Zhu
authors.forename: Shunsuke
authors.initials: S
authors.lastname: Chiba
mesh_terms: D000577:Amides / Q000138:chemical synthesis*; D001386:Azides / Q000737:chemistry*; D001391:Azo Compounds / Q000737:chemistry*; D015394:Molecular Structure; D009570:Nitriles / Q000737:chemistry*; D014753:Vinyl Compounds / Q000737:chemistry*
chemical_list: D000577:Amides; D001386:Azides; D001391:Azo Compounds; D009570:Nitriles; D014753:Vinyl Compounds
keywords: amides; nitrilium ions; nucleophilic attack; rearrangement; vinyl azides