jo6b01248_si_001.pdf (4.73 MB)
Air-Stable Pd Catalytic Systems for Sequential One-Pot Synthesis of Challenging Unsymmetrical Aminoaromatics
journal contribution
posted on 2016-07-27, 00:00 authored by Janah Shaya, Marie-Angélique Deschamps, Benoît Y. Michel, Alain BurgerThe
selective functionalization of dibromoaromatic scaffolds using
air-stable palladium catalytic systems was carried out. This methodology
involved rapid mono and diselective Buchwald-Hartwig aminations via
microwave irradiation. The conditions were optimized to couple sequentially
different moieties in one pot. Couplings with a wide scope of amines
allowed accessing a new library of symmetrical and unsymmetrical derivatives
(35 examples). Using this versatile method, a near-IR push–pull
sensor was prepared installing the electron-donating and -withdrawing
groups through a multicomponent reaction. These conditions revealed
to be gram-scalable and adaptable to various groups; hence, promoting
facile use in synthetic chemistry.