Acetic acid-catalyzed synthesis of 1,5-disubstituted 1,2,3-triazoles under azide-free conditions†

IF 4.7 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Chemistry Frontiers Pub Date : 2024-12-18 DOI:10.1039/D4QO02118E

Jiuling Li, Xinyu Jia, Qiangguo Yang, Jiakang Guo, Qianhui Ren, Taichen Liu, Kai Wei and Zhenghui Kang

引用次数: 0

Abstract

An environmentally-friendly and safe method has been developed to synthesize 1,5-disubstituted 1,2,3-triazoles containing difluoromethyl fragments, which can be obtained from readily available 2,2-difluoroarylethylamines under azide-free conditions. The classic conversion mode of acetic acid with tert-butyl nitrite is the critical factor in this reaction, allowing the diazo species generated in situ to immediately react with the raw materials to give the desired products in good yields. The mild reaction conditions and convenient operation not only make such an approach an attractive alternative method for the synthesis of polysubstituted 1,2,3-triazoles but also further promote the applications of 2,2-difluoroarylethylamines in organic synthesis.

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无叠氮条件下醋酸催化合成1,5-二取代1,2,3-三唑

在无叠氮化物的条件下，利用现成的2,2-二氟芳基乙胺可合成含有二氟甲基片段的1,5-二取代1,2,3-三唑，这是一种环境友好、安全的合成方法。醋酸与亚硝基叔丁酯的经典转化模式是反应的关键因素，使原位生成的重氮物质立即与原料反应，以良好的产率得到所需的产物。该方法反应条件温和，操作方便，不仅为多取代1,2,3-三唑的合成提供了一种有吸引力的替代方法，而且进一步促进了2,2-二氟芳基乙胺在有机合成中的应用。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Organic Chemistry Frontiers CHEMISTRY, ORGANIC-

CiteScore

7.90

自引率

11.10%

发文量

686

审稿时长

1 months

期刊介绍： Organic Chemistry Frontiers is an esteemed journal that publishes high-quality research across the field of organic chemistry. It places a significant emphasis on studies that contribute substantially to the field by introducing new or significantly improved protocols and methodologies. The journal covers a wide array of topics which include, but are not limited to, organic synthesis, the development of synthetic methodologies, catalysis, natural products, functional organic materials, supramolecular and macromolecular chemistry, as well as physical and computational organic chemistry.