posted on 2022-04-20, 14:09authored byJoseph
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).