Azide–alkyne cycloaddition (click) reaction in biomass-derived solvent CyreneTM under one-pot conditions
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 pr...
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| Format: | Article |
| Language: | English |
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Beilstein-Institut
2025-07-01
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| Series: | Beilstein Journal of Organic Chemistry |
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| Online Access: | https://doi.org/10.3762/bjoc.21.117 |
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| author | Zoltán Medgyesi László T. Mika |
| author_facet | Zoltán Medgyesi László T. Mika |
| author_sort | Zoltán Medgyesi |
| collection | DOAJ |
| description | 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. |
| format | Article |
| id | doaj-art-ea8e98350e3b4db4a48f4fa38d2dc13a |
| institution | Kabale University |
| issn | 1860-5397 |
| language | English |
| publishDate | 2025-07-01 |
| publisher | Beilstein-Institut |
| record_format | Article |
| series | Beilstein Journal of Organic Chemistry |
| spelling | doaj-art-ea8e98350e3b4db4a48f4fa38d2dc13a2025-08-20T03:42:41ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972025-07-012111544155110.3762/bjoc.21.1171860-5397-21-117Azide–alkyne cycloaddition (click) reaction in biomass-derived solvent CyreneTM under one-pot conditionsZoltán Medgyesi0László T. Mika1Department of Chemical and Environmental Process Engineering, Faculty of Chemical Technology and Biotechnology, Budapest University of Technology and Economics, Műegyetem rkp. 3., H-1111, Budapest, Hungary Department of Chemical and Environmental Process Engineering, Faculty of Chemical Technology and Biotechnology, Budapest University of Technology and Economics, Műegyetem rkp. 3., H-1111, Budapest, Hungary 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.https://doi.org/10.3762/bjoc.21.117alternative solventclick chemistrycycloadditioncyrenetm1,2,3-triazoles |
| spellingShingle | Zoltán Medgyesi László T. Mika Azide–alkyne cycloaddition (click) reaction in biomass-derived solvent CyreneTM under one-pot conditions Beilstein Journal of Organic Chemistry alternative solvent click chemistry cycloaddition cyrenetm 1,2,3-triazoles |
| title | Azide–alkyne cycloaddition (click) reaction in biomass-derived solvent CyreneTM under one-pot conditions |
| title_full | Azide–alkyne cycloaddition (click) reaction in biomass-derived solvent CyreneTM under one-pot conditions |
| title_fullStr | Azide–alkyne cycloaddition (click) reaction in biomass-derived solvent CyreneTM under one-pot conditions |
| title_full_unstemmed | Azide–alkyne cycloaddition (click) reaction in biomass-derived solvent CyreneTM under one-pot conditions |
| title_short | Azide–alkyne cycloaddition (click) reaction in biomass-derived solvent CyreneTM under one-pot conditions |
| title_sort | azide alkyne cycloaddition click reaction in biomass derived solvent cyrenetm under one pot conditions |
| topic | alternative solvent click chemistry cycloaddition cyrenetm 1,2,3-triazoles |
| url | https://doi.org/10.3762/bjoc.21.117 |
| work_keys_str_mv | AT zoltanmedgyesi azidealkynecycloadditionclickreactioninbiomassderivedsolventcyrenetmunderonepotconditions AT laszlotmika azidealkynecycloadditionclickreactioninbiomassderivedsolventcyrenetmunderonepotconditions |