Nickel-Catalyzed C–N Cross-Coupling of 4-Chloro-1,8-naphthalimides and Bulky, Primary Alkylamines at Room Temperature
Joseph P. Tassone, Travis Lundrigan, Trent D. Ashton, Mark Stradiotto
Abstract
4-Amino-1,8-naphthalimides, potentially useful fluorescent probes in biological applications, are prepared via Ni(cod)2/IPr-catalyzed cross-couplings between 4-chloro-1,8-naphthalimide electrophiles and α,α,α-trisubstituted, primary alkylamines at room temperature. This method represents the first synthesis of 4-amino-1,8-naphthalimides using Ni-catalyzed C–N cross-coupling and provides the first examples of 4-amino-1,8-naphthalimides incorporating such bulky primary alkylamines, thereby highlighting the utility of Ni-catalyzed processes in synthesizing naphthalimide scaffolds that were inaccessible using established methods (SNAr; Pd or Cu catalysis).
Topics & Concepts
ChemistryCatalysisElectrophilePrimary (astronomy)Combinatorial chemistryNickelFluorescenceNucleophilic aromatic substitutionOrganic chemistryNucleophilic substitutionPhysicsQuantum mechanicsAstronomyCatalytic C–H Functionalization MethodsCatalytic Cross-Coupling ReactionsCoordination Chemistry and Organometallics