利用芳偶氮硫代甲酰胺配体配合物催化铜(I)炔叠氮化环加成（CuAAC）

IF 2.2 3区化学 Q2 CHEMISTRY, ORGANIC

Tetrahedron Pub Date : 2025-07-23 DOI:10.1016/j.tet.2025.134860

Rabina Pradhan , Caleb Zando , Laxmi Tiwari , Sydney Schoth , Elliott B. Hulley , Kristopher V. Waynant

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引用次数: 0

摘要

偶氮甲酰胺（ATF）配体通过1,3-重氮硫羰基部分与铜(I)盐快速配位，形成稳定的铜(I)配合物。本研究以对甲氧基苯基偶氮甲酰胺（p-MeOATF）配体和碘化铜(I)为催化剂，制备了一种二聚体配合物，用于三组分铜(I)炔叠氮环加成（CuAAC）反应。反应优化表明，以2 mol%的[(p-MeOATF)CuI]2配合物和1.2 mol / l的烷基卤化物和叠氮化钠在1:1的水/甲醇溶剂中反应24 h，得到了11个产率在60 - 93%之间的1,2,3-三唑产品。由于已知ATFs可以氧化去除材料中的金属，因此在药物rufinamide的正式合成过程中对铜的去除进行了测试，为限制CuAAC反应产物中的铜含量提供了一种有前途的方法。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

Catalytic copper(I) alkyne-azide cycloaddition (CuAAC) utilizing arylazothioformamide ligand complexes

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Catalytic copper(I) alkyne-azide cycloaddition (CuAAC) utilizing arylazothioformamide ligand complexes

Azothioformamide (ATF) ligands have been shown to rapidly coordinate with copper(I) salts through a 1,3-diazothiocarbonyl moiety to form stable copper(I) complexes. In this work, a dimeric complex derived from p-methoxyphenyl azothioformamide (p-MeOATF) ligands and copper(I) iodide was employed as a catalyst for an aqueous three component copper(I) alkyne-azide cycloaddition (CuAAC) reaction. Reaction optimization identified that using 2 mol% of the [(p-MeOATF)CuI]₂ complex and 1.2 equiv. each of the alkyl halide and sodium azide in 1:1 water/methanol as solvent for 24 h gave high yields of 1,2,3-triazole products with 11 examples ranging in yields of 60–93 %. As ATFs are known to oxidatively remove metals from materials, the removal of copper during the formal synthesis of the pharmaceutical rufinamide was tested as to offer a promising approach to limiting copper content in CuAAC reaction products.

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来源期刊

Tetrahedron 化学-有机化学

CiteScore

3.90

自引率

4.80%

发文量

439

审稿时长

34 days

期刊介绍： Tetrahedron publishes full accounts of research having outstanding significance in the broad field of organic chemistry and its related disciplines, such as organic materials and bio-organic chemistry. Regular papers in Tetrahedron are expected to represent detailed accounts of an original study having substantially greater scope and details than that found in a communication, as published in Tetrahedron Letters. Tetrahedron also publishes thematic collections of papers as special issues and ''Reports'', commissioned in-depth reviews providing a comprehensive overview of a research area.