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Benzimidazole and Related Ligands for Cu-Catalyzed Azide-Alkyne Cycloaddition

Valentin O. Rodionov, Stanislav I. Presolski, Sean Gardinier, Yeon-Hee Lim and M. G. Finn*

*Department of Chemistry and The Skaggs Institute of Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, Email: mgfinnscripps.edu

V. O. Rodionov, S. I. Presolski, S. Gardinier, Y.-H. Lim, M. G. Finn, J. Am. Chem. Soc., 2007, 129, 12696-12704.

DOI: 10.1021/ja072678l (free Supporting Information)


Abstract

Tris(2-benzimidazolylmethyl)amines are superior accelerating ligands for the copper(I)-catalyzed azide-alkyne cycloaddition reaction. The water-soluble ligand (BimC4A)3 was found to be especially convenient for the rapid and high-yielding synthesis of several functionalized triazoles with 0.01-0.5 mol % Cu.

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Key Words

Triazoles, Click Chemistry


ID: J48-Y2007-3420