Direct conversion of N-alkoxyamides to carboxylic esters through tandem NBS-mediated oxidative homocoupling and thermal denitrogenation.
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.
Tianjin Key Laboratory for Modern Drug Delivery & High-Efficiency, School of Pharmaceutical Science and Technology, Tianjin University, Tianjin 300072, China.
Ningning
N
Zhang
Rui
R
Yang
Daisy
D
Zhang-Negrerie
Yunfei
Y
Du
Kang
K
Zhao
D000577:Amides / Q000737:chemistry*; D001557:Benzenesulfonates / Q000737:chemistry*; D002264:Carboxylic Acids / Q000138:chemical synthesis* / Q000737:chemistry; D004952:Esters / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010084:Oxidation-Reduction; D013696:Temperature
D000577:Amides; D001557:Benzenesulfonates; D002264:Carboxylic Acids; D004952:Esters; C081297:4-nitrobenzenesulfonate