Palladium-catalyzed annulation and intermolecular hydroamination involving norbornene derivatives: synthesis of indanones and N-alkylamines

Abstract

A palladium-catalyzed divergent reaction of primary benzamides using norbornene (NBE) derivatives as a controlled switch is reported. When NBE is used as a mediator, indanones are synthesized with moderate to good yields via a Catellani reaction that involves sequential ortho-C–H alkylation and ipso-C–N bond cleavage annulation of primary benzamides. Employing norbornadiene (NBD) instead of NBE enables the assembly of N-alkylamines by an intermolecular hydroamination reaction.