Synthesis of Triazole Click Ligands for Suzuki-Miyaura Cross-Coupling of Aryl Chlorides

Abstract

A series of new triazole ligands has been synthesized via copper-catalyzed cycloaddition reaction of readily available azides and alkynes. The synthesized compounds were characterized by FTIR, ¹H and ¹³C NMR, and high-resolution mass spectra. The ligands provided excellent yields (up to 92%) in the palladium-catalyzed Suzuki-Miyaura cross coupling of unactivated aryl chlorides with phenylboronic acid. 1-Benzyl-4-(2,6-dimethoxyphenyl)-lH-1,2,3-triazole was found to be the most effective ligand due to the presence of electron-donating 2,6-dimethoxyphenyl substituent, which made it possible to develop a highly active ligand-catalyst system for the Suzuki reaction of aryl chlorides.