Air-Stable Pd Catalytic Systems for Sequential One-Pot Synthesis of Challenging Unsymmetrical Aminoaromatics
journal contributionposted on 27.07.2016, 00:00 by Janah Shaya, Marie-Angélique Deschamps, Benoît Y. Michel, Alain Burger
The 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.