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

• Published in: Russian journal of organic chemistry Vol. 55; no. 9; pp. 1416 - 1422
• Main Authors: Jabeen, S., Khera, R. A., Iqbal, J., Asgher, M.
• Format: Journal Article
• Language: English
• Published: Moscow Pleiades Publishing 01.09.2019; Springer Nature; Springer Nature B.V
• Subjects: Alkynes; Aromatic compounds; Chemical reactions; Chemical synthesis; Chemistry; Chemistry and Materials Science; Chemistry, Organic; Chlorides; Cross coupling; Cycloaddition; Ligands; Mass spectra; NMR; Nuclear magnetic resonance; Organic Chemistry; Palladium; Physical Sciences; Science & Technology; Triazoles; Suzuki-Miyaura cross coupling; triazoles; aryl chlorides; azide-alkyne cycloaddition; palladium-catalyzed reaction; click reaction; REACTIVITY; AZIDE; BASE; 1,2,3-TRIAZOLES; CYCLOADDITIONS; CHEMISTRY; CATALYSTS
• ISSN: 1070-4280; 1608-3393
• DOI: 10.1134/S1070428019090239

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, 1 H and 13 C 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)-l H -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.