P III /P V =O Catalyzed Cascade Synthesis of N‐Functionalized Azaheterocycles
© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim An organocatalytic method for the modular synthesis of diverse N-aryl and N-alkyl azaheterocycles (indoles, oxindoles, benzimidazoles, and quinoxalinediones) is reported. The method employs a small-ring organophosphorus-based catalyst (1,2,2,3,...
| Main Authors: | , , , , |
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| Format: | Article |
| Language: | English |
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Wiley
2021
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| Online Access: | https://hdl.handle.net/1721.1/136626 |
| _version_ | 1811094694256443392 |
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| author | Nykaza, Trevor V Li, Gen Yang, Junyu Luzung, Michael R Radosevich, Alexander T |
| author2 | Massachusetts Institute of Technology. Department of Chemistry |
| author_facet | Massachusetts Institute of Technology. Department of Chemistry Nykaza, Trevor V Li, Gen Yang, Junyu Luzung, Michael R Radosevich, Alexander T |
| author_sort | Nykaza, Trevor V |
| collection | MIT |
| description | © 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim An organocatalytic method for the modular synthesis of diverse N-aryl and N-alkyl azaheterocycles (indoles, oxindoles, benzimidazoles, and quinoxalinediones) is reported. The method employs a small-ring organophosphorus-based catalyst (1,2,2,3,4,4-hexamethylphosphetane P-oxide) and a hydrosilane reductant to drive the conversion of ortho-functionalized nitroarenes into azaheterocycles through sequential intermolecular reductive C−N cross coupling with boronic acids, followed by intramolecular cyclization. This method enables the rapid construction of azaheterocycles from readily available building blocks, including a regiospecific approach to N-substituted benzimidazoles and quinoxalinediones. |
| first_indexed | 2024-09-23T16:03:34Z |
| format | Article |
| id | mit-1721.1/136626 |
| institution | Massachusetts Institute of Technology |
| language | English |
| last_indexed | 2024-09-23T16:03:34Z |
| publishDate | 2021 |
| publisher | Wiley |
| record_format | dspace |
| spelling | mit-1721.1/1366262023-01-11T18:45:27Z P III /P V =O Catalyzed Cascade Synthesis of N‐Functionalized Azaheterocycles Nykaza, Trevor V Li, Gen Yang, Junyu Luzung, Michael R Radosevich, Alexander T Massachusetts Institute of Technology. Department of Chemistry © 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim An organocatalytic method for the modular synthesis of diverse N-aryl and N-alkyl azaheterocycles (indoles, oxindoles, benzimidazoles, and quinoxalinediones) is reported. The method employs a small-ring organophosphorus-based catalyst (1,2,2,3,4,4-hexamethylphosphetane P-oxide) and a hydrosilane reductant to drive the conversion of ortho-functionalized nitroarenes into azaheterocycles through sequential intermolecular reductive C−N cross coupling with boronic acids, followed by intramolecular cyclization. This method enables the rapid construction of azaheterocycles from readily available building blocks, including a regiospecific approach to N-substituted benzimidazoles and quinoxalinediones. 2021-10-27T20:36:19Z 2021-10-27T20:36:19Z 2020 2021-03-10T14:00:09Z Article http://purl.org/eprint/type/JournalArticle https://hdl.handle.net/1721.1/136626 en 10.1002/ANIE.201914851 Angewandte Chemie - International Edition Creative Commons Attribution-Noncommercial-Share Alike http://creativecommons.org/licenses/by-nc-sa/4.0/ application/pdf Wiley PMC |
| spellingShingle | Nykaza, Trevor V Li, Gen Yang, Junyu Luzung, Michael R Radosevich, Alexander T P III /P V =O Catalyzed Cascade Synthesis of N‐Functionalized Azaheterocycles |
| title | P III /P V =O Catalyzed Cascade Synthesis of N‐Functionalized Azaheterocycles |
| title_full | P III /P V =O Catalyzed Cascade Synthesis of N‐Functionalized Azaheterocycles |
| title_fullStr | P III /P V =O Catalyzed Cascade Synthesis of N‐Functionalized Azaheterocycles |
| title_full_unstemmed | P III /P V =O Catalyzed Cascade Synthesis of N‐Functionalized Azaheterocycles |
| title_short | P III /P V =O Catalyzed Cascade Synthesis of N‐Functionalized Azaheterocycles |
| title_sort | p iii p v o catalyzed cascade synthesis of n functionalized azaheterocycles |
| url | https://hdl.handle.net/1721.1/136626 |
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