N-(Benzyloxy)-N-(pivaloyloxy)-4-(trifluoromethyl)-benzamide

CAS 2648454-31-1, Cat. No EN300-33050767

Reagent for deamination and skeletal editing of molecules

N-(Benzyloxy)-N-(pivaloyloxy)-4-(trifluoromethyl)-benzamide is the unique reagent that enables skeletal editing of molecules through direct nitrogen deletion of secondary amines. This anomeric amide is a low-temperature-melting yellow solid, which is stable under mild conditions (0 °C). The reaction with secondary amines using this reagent follows a simple procedure, resulting in the liberation of nitrogen gas and forming a C-C bond between the amine substituents. Remarkably, this transformation exhibits an extensive tolerance to various functional groups, allowing for reactions in the presence of hydroxy, ethers, tertiary amines, thioethers, and protected secondary and primary amines. Also, this reagent enables the functionalization of primary amines, for example, deamination and halogenation in a single pot. This capability significantly expands the synthetic possibilities and chemistry associated with primary amines.

Synonyms: Propanoic acid, 2,2-dimethyl-, (phenylmethoxy)[4-(trifluoromethyl)benzoyl]azanyl ester, (Phenylmethoxy)[4-(trifluoromethyl)benzoyl]azanyl 2,2-dimethylpropanoate