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

作者：Zhang Ningning; Yang Rui; Zhang Negrerie Daisy; Du Yunfei^*; Zhao Kang

来源：Journal of Organic Chemistry, 2013, 78(17): 8705-8711.

DOI：10.1021/jo401435v

Treatment of N-alkoxyamides with NBS in toluene was found to conveniently afford the corresponding carboxylic esters, including those bearing a bulky or long-chain substituent, in satisfactory to excellent yields. This approach not only represents a convenient and economic approach to a direct transformation of an alkoxyamide moiety into the carboxylic ester functional group, via oxidative homocoupling and the subsequent thermal denitrogenation, but also facilitates the synthesis of sterically hindered carboxylic esters.

• 出版日期2013-9-6
• 单位天津大学