Coupling of amides with ketones via C–N/C–H bond cleavage: a mild synthesis of 1,3-diketones

Abstract

A variety of aryl and alkyl-substituted tertiary amides react with ketones in the presence of LiHMDS and a variety of primary and secondary amides in one pot to give the corresponding 1,3-diketone products in good to excellent yields via C–N cleavage of amides and deprotonation of ketones. The reaction was conducted at room temperature under transition-metal-free conditions. N-Tosyl-, N-triflyl-, N-mesyl-, and N-Boc-substituted tertiary amides including N-benzoyl saccharin and N-benzoyl succinimide showed good activity in the reaction. The broad scope, good functional group tolerance of substrates and gram-scale synthesis showed the great importance and potential of this protocol in organic synthesis and industrial manufacture.