Stereoselective Approach to Hydroxyalkyl-1,2,3-triazoles Containing Cyclooctane Core and Their Use for CuAAC Catalysis
1,2,3-Triazoles bearing additional functional groups have found applications as the ligands in catalysis of a broad scope of reactions, synthesis of transition metals complexes for various practicable purposes, and design of metal-based drugs. Triazolyl ligands accelerating CuAAC reactions, such as...
| Main Authors: | , , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2023-05-01
|
| Series: | Catalysts |
| Subjects: | |
| Online Access: | https://www.mdpi.com/2073-4344/13/5/835 |
| _version_ | 1797600745034350592 |
|---|---|
| author | Olga V. Ryzhikova Kseniya N. Sedenkova Sergey V. Kositov Victor A. Tafeenko Yuri K. Grishin Elena B. Averina |
| author_facet | Olga V. Ryzhikova Kseniya N. Sedenkova Sergey V. Kositov Victor A. Tafeenko Yuri K. Grishin Elena B. Averina |
| author_sort | Olga V. Ryzhikova |
| collection | DOAJ |
| description | 1,2,3-Triazoles bearing additional functional groups have found applications as the ligands in catalysis of a broad scope of reactions, synthesis of transition metals complexes for various practicable purposes, and design of metal-based drugs. Triazolyl ligands accelerating CuAAC reactions, such as TBTA and TTTA, are nowadays commonly used in organic synthesis, and the search for novel ligands with a less complicated structure represents an important task. In the present work a series of hydroxyalkyltriazoles, containing a cyclooctane core, were synthesized via cycloaddition of readily available individual diastereomers of azidoalcohols or diazidodiols with phenylacetylene. The obtained hydroxyalkyltriazoles were probed as ligands for CuAAC reactions of benzyl azide with acetylenes, and 1-[(4-phenyl-1<i>H</i>-1,2,3-triazol-1-yl)methyl]cyclooctanol was demonstrated to act as an effective ligand for these processes. The complex salt of the abovementioned triazole and CuCl<sub>2</sub> was readily obtained. According to X-ray diffraction analysis data, the complex contained two molecules of triazole, in which only N1-atoms of the triazole ring acted as coordination centers. Such a molecular structure correlates well with the efficiency of 1-[(4-phenyl-1<i>H</i>-1,2,3-triazol-1-yl)methyl]cyclooctanol as a ligand in CuAAC reactions: it is able to coordinate copper ions and, at the same time, it forms a sufficiently labile complex to not withdraw copper ions from the catalytic cycle. |
| first_indexed | 2024-03-11T03:52:15Z |
| format | Article |
| id | doaj.art-ecd17cb8447047eebd3336a25bb241af |
| institution | Directory Open Access Journal |
| issn | 2073-4344 |
| language | English |
| last_indexed | 2024-03-11T03:52:15Z |
| publishDate | 2023-05-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Catalysts |
| spelling | doaj.art-ecd17cb8447047eebd3336a25bb241af2023-11-18T00:50:53ZengMDPI AGCatalysts2073-43442023-05-0113583510.3390/catal13050835Stereoselective Approach to Hydroxyalkyl-1,2,3-triazoles Containing Cyclooctane Core and Their Use for CuAAC CatalysisOlga V. Ryzhikova0Kseniya N. Sedenkova1Sergey V. Kositov2Victor A. Tafeenko3Yuri K. Grishin4Elena B. Averina5Department of Chemistry, Lomonosov Moscow State University, Leninskie Gory 1-3, 119991 Moscow, RussiaDepartment of Chemistry, Lomonosov Moscow State University, Leninskie Gory 1-3, 119991 Moscow, RussiaDepartment of Chemistry, Lomonosov Moscow State University, Leninskie Gory 1-3, 119991 Moscow, RussiaDepartment of Chemistry, Lomonosov Moscow State University, Leninskie Gory 1-3, 119991 Moscow, RussiaDepartment of Chemistry, Lomonosov Moscow State University, Leninskie Gory 1-3, 119991 Moscow, RussiaDepartment of Chemistry, Lomonosov Moscow State University, Leninskie Gory 1-3, 119991 Moscow, Russia1,2,3-Triazoles bearing additional functional groups have found applications as the ligands in catalysis of a broad scope of reactions, synthesis of transition metals complexes for various practicable purposes, and design of metal-based drugs. Triazolyl ligands accelerating CuAAC reactions, such as TBTA and TTTA, are nowadays commonly used in organic synthesis, and the search for novel ligands with a less complicated structure represents an important task. In the present work a series of hydroxyalkyltriazoles, containing a cyclooctane core, were synthesized via cycloaddition of readily available individual diastereomers of azidoalcohols or diazidodiols with phenylacetylene. The obtained hydroxyalkyltriazoles were probed as ligands for CuAAC reactions of benzyl azide with acetylenes, and 1-[(4-phenyl-1<i>H</i>-1,2,3-triazol-1-yl)methyl]cyclooctanol was demonstrated to act as an effective ligand for these processes. The complex salt of the abovementioned triazole and CuCl<sub>2</sub> was readily obtained. According to X-ray diffraction analysis data, the complex contained two molecules of triazole, in which only N1-atoms of the triazole ring acted as coordination centers. Such a molecular structure correlates well with the efficiency of 1-[(4-phenyl-1<i>H</i>-1,2,3-triazol-1-yl)methyl]cyclooctanol as a ligand in CuAAC reactions: it is able to coordinate copper ions and, at the same time, it forms a sufficiently labile complex to not withdraw copper ions from the catalytic cycle.https://www.mdpi.com/2073-4344/13/5/835CuAACazidestriazolescyclooctanesligandsX-ray |
| spellingShingle | Olga V. Ryzhikova Kseniya N. Sedenkova Sergey V. Kositov Victor A. Tafeenko Yuri K. Grishin Elena B. Averina Stereoselective Approach to Hydroxyalkyl-1,2,3-triazoles Containing Cyclooctane Core and Their Use for CuAAC Catalysis Catalysts CuAAC azides triazoles cyclooctanes ligands X-ray |
| title | Stereoselective Approach to Hydroxyalkyl-1,2,3-triazoles Containing Cyclooctane Core and Their Use for CuAAC Catalysis |
| title_full | Stereoselective Approach to Hydroxyalkyl-1,2,3-triazoles Containing Cyclooctane Core and Their Use for CuAAC Catalysis |
| title_fullStr | Stereoselective Approach to Hydroxyalkyl-1,2,3-triazoles Containing Cyclooctane Core and Their Use for CuAAC Catalysis |
| title_full_unstemmed | Stereoselective Approach to Hydroxyalkyl-1,2,3-triazoles Containing Cyclooctane Core and Their Use for CuAAC Catalysis |
| title_short | Stereoselective Approach to Hydroxyalkyl-1,2,3-triazoles Containing Cyclooctane Core and Their Use for CuAAC Catalysis |
| title_sort | stereoselective approach to hydroxyalkyl 1 2 3 triazoles containing cyclooctane core and their use for cuaac catalysis |
| topic | CuAAC azides triazoles cyclooctanes ligands X-ray |
| url | https://www.mdpi.com/2073-4344/13/5/835 |
| work_keys_str_mv | AT olgavryzhikova stereoselectiveapproachtohydroxyalkyl123triazolescontainingcyclooctanecoreandtheiruseforcuaaccatalysis AT kseniyansedenkova stereoselectiveapproachtohydroxyalkyl123triazolescontainingcyclooctanecoreandtheiruseforcuaaccatalysis AT sergeyvkositov stereoselectiveapproachtohydroxyalkyl123triazolescontainingcyclooctanecoreandtheiruseforcuaaccatalysis AT victoratafeenko stereoselectiveapproachtohydroxyalkyl123triazolescontainingcyclooctanecoreandtheiruseforcuaaccatalysis AT yurikgrishin stereoselectiveapproachtohydroxyalkyl123triazolescontainingcyclooctanecoreandtheiruseforcuaaccatalysis AT elenabaverina stereoselectiveapproachtohydroxyalkyl123triazolescontainingcyclooctanecoreandtheiruseforcuaaccatalysis |