Secondary amides are a class of highly stable compounds serving as versatile starting materials,intermediates and directing groups（amido groups） in organic synthesis.The direct deacylation of secondary amides to rel...Secondary amides are a class of highly stable compounds serving as versatile starting materials,intermediates and directing groups（amido groups） in organic synthesis.The direct deacylation of secondary amides to release amines is an important transformation in organic synthesis.Here,we report a protocol for the deacylation of secondary amides and isolation of amines.The method is based on the activation of amides with Tf_2O.followed by addition of organocerium reagents,and acidic work-up.The reaction proceeded under mild conditions and afforded the corresponding amines,isolated as their hydrochloride salts,in good yields.In combination with the C-H activation functionalization methodology,the method is applicable to the functionalization of aniline as well as conversion of carboxylic derivatives to functionalized ketones.展开更多
基金financial support from the National Natural Science Foundation of China(No.21332007)the Program for Changjiang Scholars and Innovative Research Team in University(PCSIRT) of Ministry of Education+1 种基金the Fundamental Research Funds for the Central Universities(No.20720150044)the Natural Science Foundation of Fujian Province of China (No.2014J01062)
文摘Secondary amides are a class of highly stable compounds serving as versatile starting materials,intermediates and directing groups（amido groups） in organic synthesis.The direct deacylation of secondary amides to release amines is an important transformation in organic synthesis.Here,we report a protocol for the deacylation of secondary amides and isolation of amines.The method is based on the activation of amides with Tf_2O.followed by addition of organocerium reagents,and acidic work-up.The reaction proceeded under mild conditions and afforded the corresponding amines,isolated as their hydrochloride salts,in good yields.In combination with the C-H activation functionalization methodology,the method is applicable to the functionalization of aniline as well as conversion of carboxylic derivatives to functionalized ketones.
