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Journal of the American Chemical Society. 2007 Oct 24;129(42):12696-704. doi: 10.1021/ja072678l Q115.62025

Benzimidazole and related ligands for Cu-catalyzed azide-alkyne cycloaddition

用于铜催化叠氮化物-炔烃环加成的苯并咪唑及相关配体 翻译改进

Valentin O Rodionov  1, Stanislav I Presolski, Sean Gardinier, Yeon-Hee Lim, M G Finn

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  • 1 Department of Chemistry and The Skaggs Institute of Chemical Biology, The Scripps Research Institute, La Jolla, CA 92037, USA.
  • DOI: 10.1021/ja072678l PMID: 17914816

    摘要 Ai翻译

    Tris(2-benzimidazolylmethyl)amines have been found to be superior accelerating ligands for the copper(I)-catalyzed azide-alkyne cycloaddition reaction. Candidates bearing different benzimidazole N-substituents as well as benzothiazole and pyridyl ligand arms were evaluated by absolute rate measurements under relatively dilute conditions by aliquot quenching kinetics and by relative rate measurements under concentrated conditions by reaction calorimetry. Benzimidazole-based ligands with pendant alkylcarboxylate arms proved to be advantageous in the latter case. The catalyst system was shown to involve more than one active species, providing a complex response to changes in pH and buffer salts and the persistence of high catalytic rate in the presence of high concentrations of coordinating ligands. 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.

    Keywords:benzimidazole ligands; cu-catalyzed reaction; azide-alkyne cycloaddition

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    期刊名:Journal of the american chemical society

    缩写:J AM CHEM SOC

    ISSN:0002-7863

    e-ISSN:1520-5126

    IF/分区:15.6/Q1

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    Benzimidazole and related ligands for Cu-catalyzed azide-alkyne cycloaddition