A simple copper salt catalysed the coupling of imidazole with arylboronic acids in protic solventDedicated to Professor Xie Ming-Gui on the occasion of his 65th birthday.

Abstract

In the presence of a catalytic amount of a simple copper salt, the coupling of imidazole with arylboronic acids was performed in methanol to give corresponding N-arylimidazoles in almost quantitative yields; this coupling reaction could also be performed in aqueous solutions to give N-arylimidazoles in excellent yields.

Platinum(ii) N-heterocyclic carbene complexes: coordination and cyclometallation.

“…Imidazolium salts were synthesised via literature routes: 1a via the copper catalysed coupling of 4-fluoro-phenyl boronic acid with imidazole, 44 followed by reaction with MeI; 1b via the condensation of 4-fluoro-aniline with glyoxal, 45 followed by reaction with chloromethylethyl ether; 1c via the copper catalysed coupling of 4-fluoro-phenyl boronic acid with imidazole, followed by reaction with 4-fluoro-benzyl bromide; 1d via the reaction of methylimidazole with 4-fluoro-benzyl bromide. Silver NHC salts were then prepared via the reaction of imidazolium salt with silver oxide in DCM.…”

An Efficient N‐Arylation of Heterocycles with Aryl‐, Heteroaryl‐, and Vinylboronic Acids Catalyzed by Copper Fluorapatite

“…Later, Collman and co-workers demonstrated the use of a diamine-copper complex for the coupling of arylboronic acids with imidazole in CH 2 Cl 2 and H 2 O at room temperature [14] [15]. Very recently, the same coupling reaction was also performed by Xie and co-workers using a copper salt in protic solvents under reflux conditions without using any base [16]. Thus, the development of mild and costeffective catalytic procedures for N-arylation of imidazoles and amines still remains an active research area [17].…”

Sequential Metal‐Catalyzed N‐Heteroarylation and C–C Cross‐Coupling Reactions: An Expedient Route to Tris(hetero)aryl Systems

“…[12] A CuCl-catalyzed N-arylation of imidazole with arylboronic acids has been developed in the absence of an additional chelating ligand. [13] Combined N(1)-and C(3)-arylations of 3-iodoindazole using boronic acids and Cu(OAc) 2 have been reported. [14] However, these methods require additional steps to synthesize the arylboronic acid.…”