One-Pot Synthesis of <i>B</i>-Aryl Carboranes with Sensitive Functional Groups Using Sequential Cobalt- and Palladium-Catalyzed Reactions

One-Pot Synthesis of <i>B</i>-Aryl Carboranes with Sensitive Functional Groups Using Sequential Cobalt- and Palladium-Catalyzed Reactions

The simple and efficient method was developed for the one-pot synthesis of <i>B</i>-substituted aryl derivatives of <i>ortho</i>-carborane with functional groups sensitive to organolithium and organomagnesium reagents using 9-iodo-<i>ortho</i>-carborane and genera...

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Main Authors: Sergey A. Anufriev, Akim V. Shmal’ko, Kyrill Yu. Suponitsky, Igor B. Sivaev
Format: Article
Language:English
Published: MDPI AG 2020-11-01
Series:Catalysts
Subjects:
<i>ortho</i>-carborane
<i>B-</i>aryl derivatives
synthesis
Co/Pd catalysis
X-ray diffraction
Online Access:https://www.mdpi.com/2073-4344/10/11/1348
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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 The simple and efficient method was developed for the one-pot synthesis of <i>B</i>-substituted aryl derivatives of <i>ortho</i>-carborane with functional groups sensitive to organolithium and organomagnesium reagents using 9-iodo-<i>ortho</i>-carborane and generated in situ organozinc compounds. The method proposed was used to prepare a series of 9-aryl-<i>ortho</i>-carboranes, including those containing nitrile and ester groups, 9-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>o</i>-OMe, <i>p</i>-OMe, <i>o</i>-CN, <i>p</i>-CN, <i>o</i>-COOEt, <i>m</i>-COOEt, and <i>p</i>-COOEt). It was demonstrated that the same approach can be used for synthesis of diaryl derivatives of <i>ortho</i>-carborane 9,12-(RC<sub>6</sub>H<sub>4</sub>)<sub>2</sub>-1,2-C<sub>2</sub>B<sub>10</sub>H<sub>10</sub> (R = H, <i>p</i>-Me). The solid-state structures of 9-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>-NMe<sub>2</sub>, <i>p</i>-OCH<sub>2</sub>OMe, <i>o</i>-OMe, <i>o</i>-CN, <i>p</i>-CN, <i>m</i>-COOEt, and <i>p</i>-COOEt) and 9,12-(<i>p</i>-MeC<sub>6</sub>H<sub>4</sub>)<sub>2</sub>-1,2-C<sub>2</sub>B<sub>10</sub>H<sub>10</sub> were determined by single crystal X-ray diffraction.
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spelling doaj.art-8f3b984c1bc841408b1b2f36180b71332023-11-20T21:32:30ZengMDPI AGCatalysts2073-43442020-11-011011134810.3390/catal10111348One-Pot Synthesis of <i>B</i>-Aryl Carboranes with Sensitive Functional Groups Using Sequential Cobalt- and Palladium-Catalyzed ReactionsSergey 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, RussiaThe simple and efficient method was developed for the one-pot synthesis of <i>B</i>-substituted aryl derivatives of <i>ortho</i>-carborane with functional groups sensitive to organolithium and organomagnesium reagents using 9-iodo-<i>ortho</i>-carborane and generated in situ organozinc compounds. The method proposed was used to prepare a series of 9-aryl-<i>ortho</i>-carboranes, including those containing nitrile and ester groups, 9-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>o</i>-OMe, <i>p</i>-OMe, <i>o</i>-CN, <i>p</i>-CN, <i>o</i>-COOEt, <i>m</i>-COOEt, and <i>p</i>-COOEt). It was demonstrated that the same approach can be used for synthesis of diaryl derivatives of <i>ortho</i>-carborane 9,12-(RC<sub>6</sub>H<sub>4</sub>)<sub>2</sub>-1,2-C<sub>2</sub>B<sub>10</sub>H<sub>10</sub> (R = H, <i>p</i>-Me). The solid-state structures of 9-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>-NMe<sub>2</sub>, <i>p</i>-OCH<sub>2</sub>OMe, <i>o</i>-OMe, <i>o</i>-CN, <i>p</i>-CN, <i>m</i>-COOEt, and <i>p</i>-COOEt) and 9,12-(<i>p</i>-MeC<sub>6</sub>H<sub>4</sub>)<sub>2</sub>-1,2-C<sub>2</sub>B<sub>10</sub>H<sub>10</sub> were determined by single crystal X-ray diffraction.https://www.mdpi.com/2073-4344/10/11/1348<i>ortho</i>-carborane<i>B-</i>aryl derivativessynthesisCo/Pd catalysisX-ray diffraction
spellingShingle Sergey A. Anufriev
Akim V. Shmal’ko
Kyrill Yu. Suponitsky
Igor B. Sivaev
One-Pot Synthesis of <i>B</i>-Aryl Carboranes with Sensitive Functional Groups Using Sequential Cobalt- and Palladium-Catalyzed Reactions
Catalysts
<i>ortho</i>-carborane
<i>B-</i>aryl derivatives
synthesis
Co/Pd catalysis
X-ray diffraction
title One-Pot Synthesis of <i>B</i>-Aryl Carboranes with Sensitive Functional Groups Using Sequential Cobalt- and Palladium-Catalyzed Reactions
title_full One-Pot Synthesis of <i>B</i>-Aryl Carboranes with Sensitive Functional Groups Using Sequential Cobalt- and Palladium-Catalyzed Reactions
title_fullStr One-Pot Synthesis of <i>B</i>-Aryl Carboranes with Sensitive Functional Groups Using Sequential Cobalt- and Palladium-Catalyzed Reactions
title_full_unstemmed One-Pot Synthesis of <i>B</i>-Aryl Carboranes with Sensitive Functional Groups Using Sequential Cobalt- and Palladium-Catalyzed Reactions
title_short One-Pot Synthesis of <i>B</i>-Aryl Carboranes with Sensitive Functional Groups Using Sequential Cobalt- and Palladium-Catalyzed Reactions
title_sort one pot synthesis of i b i aryl carboranes with sensitive functional groups using sequential cobalt and palladium catalyzed reactions
topic <i>ortho</i>-carborane
<i>B-</i>aryl derivatives
synthesis
Co/Pd catalysis
X-ray diffraction
url https://www.mdpi.com/2073-4344/10/11/1348
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AT kyrillyusuponitsky onepotsynthesisofibiarylcarboraneswithsensitivefunctionalgroupsusingsequentialcobaltandpalladiumcatalyzedreactions
AT igorbsivaev onepotsynthesisofibiarylcarboraneswithsensitivefunctionalgroupsusingsequentialcobaltandpalladiumcatalyzedreactions

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