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Nickel-Catalyzed C–N Cross-Coupling of 4‑Chloro-1,8-naphthalimides and Bulky, Primary Alkylamines at Room Temperature

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posted on 2022-04-20, 14:09 authored by Joseph P. Tassone, Travis Lundrigan, Trent D. Ashton, Mark Stradiotto
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).

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