Synthesis of 3-Aryl-<i>ortho</i>-carboranes with Sensitive Functional Groups
A simple and efficient method was developed for the one-pot synthesis of 3-aryl derivatives of <i>ortho</i>-carborane with sensitive functional groups using 3-iodo-<i>ortho</i>-carborane and aryl zinc bromides that were generated in situ. A series of 3-aryl-<i>ortho<...
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| Format: | Article |
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MDPI AG
2021-12-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/26/23/7297 |
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| author | Sergey A. Anufriev Akim V. Shmal’ko Kyrill Yu. Suponitsky Igor B. Sivaev |
| author_facet | Sergey A. Anufriev Akim V. Shmal’ko Kyrill Yu. Suponitsky Igor B. Sivaev |
| author_sort | Sergey A. Anufriev |
| collection | DOAJ |
| description | A simple and efficient method was developed for the one-pot synthesis of 3-aryl derivatives of <i>ortho</i>-carborane with sensitive functional groups using 3-iodo-<i>ortho</i>-carborane and aryl zinc bromides that were generated in situ. A series of 3-aryl-<i>ortho</i>-carboranes, including those containing nitrile and ester groups, 3-RC<sub>6</sub>H<sub>4</sub>-1,2-C<sub>2</sub>B<sub>10</sub>H<sub>11</sub> (R = <i>p</i>-Me, <i>p</i>-NMe<sub>2</sub>, <i>p</i>-OCH<sub>2</sub>OMe, <i>p</i>-OMe, <i>o</i>-CN, <i>p</i>-CN, <i>o</i>-COOEt, <i>m</i>-COOEt, <i>p</i>-COOEt) was synthesized using this approach. The solid-state structures of 3-RC<sub>6</sub>H<sub>4</sub>-1,2-C<sub>2</sub>B<sub>10</sub>H<sub>11</sub> (R = <i>p</i>-OMe, <i>o</i>-CN, and <i>p</i>-CN) were determined by single crystal X-ray diffraction. The intramolecular hydrogen bonding involving the <i>ortho</i>-substituents of the aryl ring and the CH and BH groups of carborane was discussed. |
| first_indexed | 2024-03-10T04:47:57Z |
| format | Article |
| id | doaj.art-fdd2539896d74b3fb662939e79643300 |
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| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-10T04:47:57Z |
| publishDate | 2021-12-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-fdd2539896d74b3fb662939e796433002023-11-23T02:50:25ZengMDPI AGMolecules1420-30492021-12-012623729710.3390/molecules26237297Synthesis of 3-Aryl-<i>ortho</i>-carboranes with Sensitive Functional GroupsSergey A. Anufriev0Akim V. Shmal’ko1Kyrill Yu. Suponitsky2Igor B. Sivaev3A.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 simple and efficient method was developed for the one-pot synthesis of 3-aryl derivatives of <i>ortho</i>-carborane with sensitive functional groups using 3-iodo-<i>ortho</i>-carborane and aryl zinc bromides that were generated in situ. A series of 3-aryl-<i>ortho</i>-carboranes, including those containing nitrile and ester groups, 3-RC<sub>6</sub>H<sub>4</sub>-1,2-C<sub>2</sub>B<sub>10</sub>H<sub>11</sub> (R = <i>p</i>-Me, <i>p</i>-NMe<sub>2</sub>, <i>p</i>-OCH<sub>2</sub>OMe, <i>p</i>-OMe, <i>o</i>-CN, <i>p</i>-CN, <i>o</i>-COOEt, <i>m</i>-COOEt, <i>p</i>-COOEt) was synthesized using this approach. The solid-state structures of 3-RC<sub>6</sub>H<sub>4</sub>-1,2-C<sub>2</sub>B<sub>10</sub>H<sub>11</sub> (R = <i>p</i>-OMe, <i>o</i>-CN, and <i>p</i>-CN) were determined by single crystal X-ray diffraction. The intramolecular hydrogen bonding involving the <i>ortho</i>-substituents of the aryl ring and the CH and BH groups of carborane was discussed.https://www.mdpi.com/1420-3049/26/23/7297<i>ortho</i>-carborane3-aryl derivativessynthesisCo/Pd catalysisX-ray diffractionintramolecular hydrogen bonds |
| spellingShingle | Sergey A. Anufriev Akim V. Shmal’ko Kyrill Yu. Suponitsky Igor B. Sivaev Synthesis of 3-Aryl-<i>ortho</i>-carboranes with Sensitive Functional Groups Molecules <i>ortho</i>-carborane 3-aryl derivatives synthesis Co/Pd catalysis X-ray diffraction intramolecular hydrogen bonds |
| title | Synthesis of 3-Aryl-<i>ortho</i>-carboranes with Sensitive Functional Groups |
| title_full | Synthesis of 3-Aryl-<i>ortho</i>-carboranes with Sensitive Functional Groups |
| title_fullStr | Synthesis of 3-Aryl-<i>ortho</i>-carboranes with Sensitive Functional Groups |
| title_full_unstemmed | Synthesis of 3-Aryl-<i>ortho</i>-carboranes with Sensitive Functional Groups |
| title_short | Synthesis of 3-Aryl-<i>ortho</i>-carboranes with Sensitive Functional Groups |
| title_sort | synthesis of 3 aryl i ortho i carboranes with sensitive functional groups |
| topic | <i>ortho</i>-carborane 3-aryl derivatives synthesis Co/Pd catalysis X-ray diffraction intramolecular hydrogen bonds |
| url | https://www.mdpi.com/1420-3049/26/23/7297 |
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