Palladium-catalyzed ligand-free and aqueous Suzuki reaction for the construction of (hetero)aryl-substituted triphenylamine derivatives?

RSC Advances Pub Date: 2012-11-06 DOI: 10.1039/C2RA22275B

Abstract

This paper reports an efficient synthesis of triphenylamine (TPA) derivatives via a palladium-catalyzed Suzuki reaction of (hetero)aryl halides with 4-(diphenylamino)phenylboronic acid (DPBA) in aqueous ethanol under aerobic and ligand-free conditions. Heteroaryl halides, namely pyridyl bromides, quinolyl bromides, pyrimidinyl bromides, 2-chloropyrazine and sulfur-containing heteroaryl bromides, could react smoothly with DPBA, affording good to excellent yields under mild conditions. In addition, aryl bromides were also successfully employed in the cross-couplings with DPBA and furnished the products in high yields at room temperature. The cross-coupling of 4-bromobenzonitrile with DPBA gave the desired product in a quantitative yield within 2 min, resulting in a TOF up to 5820 h?1.

Graphical abstract: Palladium-catalyzed ligand-free and aqueous Suzuki reaction for the construction of (hetero)aryl-substituted triphenylamine derivatives
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