{"title":"Azide-alkyne cycloaddition (click) reaction in biomass-derived solvent Cyrene<sup>TM</sup> under one-pot conditions.","authors":"Zoltán Medgyesi, László T Mika","doi":"10.3762/bjoc.21.117","DOIUrl":null,"url":null,"abstract":"<p><p>It was demonstrated that Cyrene<sup>TM</sup>, as a biomass-originated polar aprotic solvent, could be utilized as an alternative reaction medium for one-pot copper(I)-catalyzed azide-alkyne cycloaddition (click or CuAAC) reactions, for the synthesis of various 1,2,3-triazoles under mild conditions. Nineteen products involving <i>N</i>-substituted-4-phenyl-1<i>H</i>-1,2,3- and 1-allyl-4-substituted-1<i>H</i>-1,2,3-triazoles were synthesized under one-pot conditions and isolated with good to excellent yields (50-96%) and purity (>98%). The observed results represent an example that proves that biomass-derived safer solvents can be introduced into a synthetically important transformation exhibiting higher chemical and environmental safety.</p>","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"21 ","pages":"1544-1551"},"PeriodicalIF":2.1000,"publicationDate":"2025-07-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC12320739/pdf/","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Beilstein Journal of Organic Chemistry","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.3762/bjoc.21.117","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"2025/1/1 0:00:00","PubModel":"eCollection","JCR":"Q2","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0
Abstract
It was demonstrated that CyreneTM, as a biomass-originated polar aprotic solvent, could be utilized as an alternative reaction medium for one-pot copper(I)-catalyzed azide-alkyne cycloaddition (click or CuAAC) reactions, for the synthesis of various 1,2,3-triazoles under mild conditions. Nineteen products involving N-substituted-4-phenyl-1H-1,2,3- and 1-allyl-4-substituted-1H-1,2,3-triazoles were synthesized under one-pot conditions and isolated with good to excellent yields (50-96%) and purity (>98%). The observed results represent an example that proves that biomass-derived safer solvents can be introduced into a synthetically important transformation exhibiting higher chemical and environmental safety.
期刊介绍：
The Beilstein Journal of Organic Chemistry is an international, peer-reviewed, Open Access journal. It provides a unique platform for rapid publication without any charges (free for author and reader) – Platinum Open Access. The content is freely accessible 365 days a year to any user worldwide. Articles are available online immediately upon publication and are publicly archived in all major repositories. In addition, it provides a platform for publishing thematic issues (theme-based collections of articles) on topical issues in organic chemistry.
The journal publishes high quality research and reviews in all areas of organic chemistry, including organic synthesis, organic reactions, natural product chemistry, structural investigations, supramolecular chemistry and chemical biology.
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