Mild N-deacylation of secondary amides by alkylation with organocerium reagents

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 Tf2O, 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 CH activation functionalization methodology, the method is applicable to the functionalization of aniline as well as conversion of carboxylic derivatives to functionalized ketones.

Graphical abstractUsing organocerium reagents as alkylation reagents, the deprotection of secondary amides were achieved under mild conditions to yield the corresponding amine hydrochloride salts in good yields.Figure optionsDownload full-size imageDownload as PowerPoint slide