Cu(BF₄)₂/AC-Catalyzed Synthesis of N-Substituted Anilines, N-Substituted 1,6-Naphthyridin-5(6H)-one, and Isoquinolin-1(2H)-one

Abstract

Herein, we report practical Cu(BF 4 ) 2 /activated carbon-catalyzed amination of various anilines, isoquinolinone, and naphthyridinone with aryl boronic acids. The ultrasonic and rotary evaporation treatment of the mixture of aq. Cu(BF 4 ) 2 and activated carbon in methanol afforded a novel Cu(II)-catalyst, which is air-stable and can be effectively applied in the Chan−Lam coupling reaction. The products of N-arylation were isolated in good to excellent yields at low catalytic loading. And Cu(BF 4 ) 2 /AC also showed good reusability.

Recent advances in Chan–Lam coupling reaction

“…Meanwhile, Zeng and co-workers developed a simple heterogeneous Cu(BF 4 ) 2 /activated carbon-catalysed Chan–Lam coupling of aryl boronic acids with C–N coupling partners such as various anilines, naphthyridinone, and isoquinolinone. 28 To create this innovative air-stable Cu(BF 4 ) 2 -AC based catalyst, the research team treated aqueous Cu(BF 4 ) 2 and the activated carbon blend via ultrasonic and rotatory evaporation operations in methanol. Firstly, they carried out the C–N coupling of various anilines with phenylboronic acids under base-free conditions in the presence of 10 mol% Cu(BF 4 ) 2 /AC and 2 equiv.…”

A chemoselective and one‐pot method for the synthesis of unsymmetrical secondary amines via coupling reaction of ammonia and aryl(alkyl) halides catalyzed by MNP@IAH@Cu‐IL as a bifunctional nanocatalyst

“…1,19,20 Among the various coupling agents, copper catalysts have received significant attention due to their economic attractiveness, good functional group tolerance, and efficiency compared with other precious transition metals. [21][22][23][24] Therefore, both homogeneous and heterogeneous Cu(I) or Cu(II) catalysts have been used in coupling reactions for the recent decades. 25,26 Heterogeneous catalytic systems are preferred from an industrial and environmental standpoint.…”