Metal-Free Aerobic Oxidative C−C Bond Cleavage between the Carbonyl Carbon and the α-Carbon of α-Azido Ketones: A Novel Synthesis of N-Alkylated Benzamides

Abstract

An unprecedented metal-free approach has been achieved for the synthesis of N-alkylated benzamides from phenacyl azides by oxidative cleavage of a C−C bond and formation of a new C−N bond in the presence of K2CO3. Various substituted phenacyl azides could be readily cleaved to access a variety of N-alkylated benzamides by using the new protocol, which is a viable alternative for the construction of amide bonds. This metal-free reaction forms amides in excellent yields with minimal generation of waste. The high functional group tolerance and diverse substrate scope make this reaction useful for organic synthesis.