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Direct Conversion of N-Alkoxyamides to Carboxylic Esters through Tandem NBS-Mediated Oxidative Homocoupling and Thermal Denitrogenation

Ningning Zhang, Rui Yang, Daisy Zhang-Negrerie, Yunfei Du* and Kang Zhao*

*Tianjin Key Laboratory for Modern Drug Delivery & High-Efficiency, School of Pharmaceutical Science and Technology, Tianjin University, Tianjin 300072, China, Email: duyunfeiertju.edu.cn, kangzhaotju.edu.cn

N. Zhang, R. Yang, D. Zhang-Negrerie, Y. Du, K. Zhao, J. Org. Chem., 2013, 78, 8705-8711.

DOI: 10.1021/jo401435v (free Supporting Information)


Abstract

N-alkoxyamides conveniently afford the corresponding carboxylic esters in the presence of NBS in toluene via oxidative homocoupling and the subsequent thermal denitrogenation. Even substrates bearing a bulky or long-chain substituent gave products in good yields in this convenient and economic approach to a direct transformation of an alkoxyamide moiety into the carboxylic ester functional group.


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Key Words

Esters, NBS


ID: J42-Y2013