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

• Published in: Asian journal of organic chemistry Vol. 6; no. 10; p. 1498
• Main Authors: Reddy, Chada Narsimha, Krishna, Namballa Hari, Reddy, V Ganga, Alarifi, Abdullah, Kamal, Ahmed
• Format: Journal Article
• Language: English
• Published: Weinheim Wiley Subscription Services, Inc 01-10-2017
• Subjects: Alkylation; Amides; Azides (organic); Carbonyls; Chemical synthesis; Cleavage; Ketones; Organic chemistry
• ISSN: 2193-5807; 2193-5815
• DOI: 10.1002/ajoc.201700329

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.