Amide synthesis by nucleophilic attack of vinyl azides

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 BF₃̇OEt₂. 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. Nitrilium intermediate: A new method for amide synthesis employs vinyl azides as enamine-type nucleophiles towards carbon electrophiles in the presence of BF₃̇OEt₂. After nucleophilic attack of the vinyl azide, a substituent of the resulting iminodiazonium ion intermediate A migrates to form nitrilium ion B, which is hydrolyzed to afford the corresponding amide.