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.
Mild and free: Metal‐free aerobic oxidative C−C bond cleavage between the carbonyl carbon and α‐carbon atoms of α‐azido ketones in the presence of base is described for the construction of new C−N bonds in the synthesis of N‐alkylated benzamides from phenacyl azides and methanamines.