Selective Synthesis of Imines by Photo-Oxidative Amine Cross-Condensation Catalyzed by PCN-222(Pd)
Aitor Bermejo‐López, Sergio Carrasco, Pedro J. Tortajada, Kenji P. M. Kopf, Amparo Sanz‐Marco, Mathias S. Hvid, Nina Lock, Belén Martín‐Matute
Abstract
Palladium-metalated PCN-222 enables the aerobic photo-oxidative cross-condensation of anilines with benzylic amines yielding a series of linear and cyclic imines. The reaction is very efficient under mild conditions, which allows the isolation of simple, yet elusive, intermediates such as 2-(benzylideneamino)aniline and 2-(benzylideneamino)phenols. Recyclability studies show excellent activity and selectivity after five runs. The methodology was successfully applied for the synthesis of an antitumor agent (PMX-610).
Topics & Concepts
AnilineChemistryPalladiumAmine gas treatingCatalysisSelectivityCondensationOxidative phosphorylationPhenolsCombinatorial chemistryCondensation reactionOrganic chemistryPhotochemistryPhysicsBiochemistryThermodynamicsCatalytic C–H Functionalization MethodsSynthesis and Biological EvaluationClick Chemistry and Applications