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.
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
作者单位 +展开
作者单位
DOI: 10.1021/ja072678l PMID: 17914816
摘要 Ai翻译
相关内容
-
Apparent copper(II)-accelerated azide-alkyne cycloaddition
看似被铜(II)加速的叠氮-炔环加成反应
Organic letters. 2009 Nov 5;11(21):4954-7.
-
A facile route to viologen functional macromolecules through azide-alkyne [3+2] cycloaddition
通过叠氮炔烃环加成方便地制备双芳基乙烯功能高分子路线
Macromolecular rapid communications. 2013 Oct;34(19):1547-53.
-
Azide alkyne cycloaddition facilitated by hexanuclear rhenium chalcogenide cluster complexes
六核铼硫属元素簇配合物促进的叠氮炔烃环加成反应
Dalton transactions (Cambridge, England : 2003). 2013 Jun 14;42(22):8132-9.
-
Regiodivergent Rhodium(I)-Catalyzed Azide-Alkyne Cycloaddition (RhAAC) To Access Either Fully Substituted Sulfonyl-1,2,3-triazoles under Mild Conditions
温和条件下通过区域选择性铑催化炔氢-叠氮加成反应合成位阻较大的磺酰基-1,4-和-1,5-三唑化合物
Organic letters. 2018 Nov 2;20(21):6705-6709.
-
Copper phosphorylated cellulose nanofibers mediated azide-alkyne cycloaddition click reaction in water
铜磷化纤维素纳米纤维介导的水相叠氮𬭩-炔烃环加成点击反应
Carbohydrate polymers. 2024 Jan 15:324:121501.
-
The effects of ionic liquids on azide-alkyne cycloaddition reactions
离子液体对叠氮化物-炔烃环加成反应的影响
Organic & biomolecular chemistry. 2010 Dec 7;8(23):5354-8.
-
The reaction mechanism of the azide-alkyne Huisgen cycloaddition
叠氮炔𬭩环加成反应的机理研究
Physical chemistry chemical physics : PCCP. 2019 Sep 11;21(35):19281-19287.
-
Ruthenium-catalyzed azide-alkyne cycloaddition: scope and mechanism
钌催化叠氮-炔烃环加成反应:作用范围与机制研究
Journal of the American Chemical Society. 2008 Jul 16;130(28):8923-30.