Synthesis of <i>B</i>-Substituted Anthracenyl and Pyrenyl Derivatives of <i>ortho</i>-Carborane
Isomeric <i>B</i>-substituted anthracenyl and pyrenyl derivatives of <i>ortho</i>-carborane containing polycyclic aromatic substituents both in the position of the carborane cage most distant from the carbon atoms (position 9) and in the neighboring position (position 3) were...
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MDPI AG
2025-04-01
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| Series: | Inorganics |
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| author | Akim V. Shmal’ko Sergey A. Anufriev Kyrill Yu. Suponitsky Evgeniia P. Antoshkina Igor B. Sivaev Vladimir I. Bregadze |
| author_facet | Akim V. Shmal’ko Sergey A. Anufriev Kyrill Yu. Suponitsky Evgeniia P. Antoshkina Igor B. Sivaev Vladimir I. Bregadze |
| author_sort | Akim V. Shmal’ko |
| collection | DOAJ |
| description | Isomeric <i>B</i>-substituted anthracenyl and pyrenyl derivatives of <i>ortho</i>-carborane containing polycyclic aromatic substituents both in the position of the carborane cage most distant from the carbon atoms (position 9) and in the neighboring position (position 3) were synthesized by Pd-catalyzed cross-coupling of the corresponding iodo derivatives of <i>ortho</i>-carborane with polycyclic aryl zinc bromides. The derivative containing two pyrenyl substituents at the positions most distant from the carbon atoms of the <i>ortho</i>-carborane cage, 9,12-di(pyren-1′-yl)-<i>ortho</i>-carborane, was obtained in a similar way starting from 9,12-diiodo-<i>ortho</i>-carborane. The solid-state structures of the pyrene-containing derivatives 3-pyren-1′-yl-<i>ortho</i>-carborane, 9-pyren-1′-yl-<i>ortho</i>-carborane, and 9,12-di(pyren-1′-yl)-<i>ortho</i>-carborane were determined by single-crystal X-ray diffraction. |
| format | Article |
| id | doaj-art-2f67ff47f0da48a48fd6874e65ae076b |
| institution | Kabale University |
| issn | 2304-6740 |
| language | English |
| publishDate | 2025-04-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Inorganics |
| spelling | doaj-art-2f67ff47f0da48a48fd6874e65ae076b2025-08-20T03:47:57ZengMDPI AGInorganics2304-67402025-04-0113513810.3390/inorganics13050138Synthesis of <i>B</i>-Substituted Anthracenyl and Pyrenyl Derivatives of <i>ortho</i>-CarboraneAkim V. Shmal’ko0Sergey A. Anufriev1Kyrill Yu. Suponitsky2Evgeniia P. Antoshkina3Igor B. Sivaev4Vladimir I. Bregadze5A.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilov Str., 119991 Moscow, RussiaA.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilov Str., 119991 Moscow, RussiaA.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilov Str., 119991 Moscow, RussiaA.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilov Str., 119991 Moscow, RussiaA.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilov Str., 119991 Moscow, RussiaA.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilov Str., 119991 Moscow, RussiaIsomeric <i>B</i>-substituted anthracenyl and pyrenyl derivatives of <i>ortho</i>-carborane containing polycyclic aromatic substituents both in the position of the carborane cage most distant from the carbon atoms (position 9) and in the neighboring position (position 3) were synthesized by Pd-catalyzed cross-coupling of the corresponding iodo derivatives of <i>ortho</i>-carborane with polycyclic aryl zinc bromides. The derivative containing two pyrenyl substituents at the positions most distant from the carbon atoms of the <i>ortho</i>-carborane cage, 9,12-di(pyren-1′-yl)-<i>ortho</i>-carborane, was obtained in a similar way starting from 9,12-diiodo-<i>ortho</i>-carborane. The solid-state structures of the pyrene-containing derivatives 3-pyren-1′-yl-<i>ortho</i>-carborane, 9-pyren-1′-yl-<i>ortho</i>-carborane, and 9,12-di(pyren-1′-yl)-<i>ortho</i>-carborane were determined by single-crystal X-ray diffraction.https://www.mdpi.com/2304-6740/13/5/138<i>ortho</i>-carboranearyl derivativesanthracenepyrenesynthesisNMR spectra |
| spellingShingle | Akim V. Shmal’ko Sergey A. Anufriev Kyrill Yu. Suponitsky Evgeniia P. Antoshkina Igor B. Sivaev Vladimir I. Bregadze Synthesis of <i>B</i>-Substituted Anthracenyl and Pyrenyl Derivatives of <i>ortho</i>-Carborane Inorganics <i>ortho</i>-carborane aryl derivatives anthracene pyrene synthesis NMR spectra |
| title | Synthesis of <i>B</i>-Substituted Anthracenyl and Pyrenyl Derivatives of <i>ortho</i>-Carborane |
| title_full | Synthesis of <i>B</i>-Substituted Anthracenyl and Pyrenyl Derivatives of <i>ortho</i>-Carborane |
| title_fullStr | Synthesis of <i>B</i>-Substituted Anthracenyl and Pyrenyl Derivatives of <i>ortho</i>-Carborane |
| title_full_unstemmed | Synthesis of <i>B</i>-Substituted Anthracenyl and Pyrenyl Derivatives of <i>ortho</i>-Carborane |
| title_short | Synthesis of <i>B</i>-Substituted Anthracenyl and Pyrenyl Derivatives of <i>ortho</i>-Carborane |
| title_sort | synthesis of i b i substituted anthracenyl and pyrenyl derivatives of i ortho i carborane |
| topic | <i>ortho</i>-carborane aryl derivatives anthracene pyrene synthesis NMR spectra |
| url | https://www.mdpi.com/2304-6740/13/5/138 |
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