Protecting-group-free ortho-C–H borylation of anilines enabled by mesoionic carbene-Ir complex
We describe an iridium-catalyzed ortho-selective C–H borylation of unprotected anilines. The employing strong σ-donating cyclometalated mesoionic carbene as C^C bidentate ligand is crucial for the high ortho-selectivity. Computational studies support outer-sphere X–H···Oboryl hydrogen bond interacti...
| Main Authors: | , , , , , |
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| Format: | Article |
| Language: | English |
| Published: |
KeAi Communications Co. Ltd.
2023-11-01
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| Series: | Green Synthesis and Catalysis |
| Subjects: | |
| Online Access: | http://www.sciencedirect.com/science/article/pii/S266655492200045X |
| _version_ | 1827395929935708160 |
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| author | Zengyu Zhang Shiqing Huang Wei Liu Liang-Liang Zhao Chubin Hu Xiaoyu Yan |
| author_facet | Zengyu Zhang Shiqing Huang Wei Liu Liang-Liang Zhao Chubin Hu Xiaoyu Yan |
| author_sort | Zengyu Zhang |
| collection | DOAJ |
| description | We describe an iridium-catalyzed ortho-selective C–H borylation of unprotected anilines. The employing strong σ-donating cyclometalated mesoionic carbene as C^C bidentate ligand is crucial for the high ortho-selectivity. Computational studies support outer-sphere X–H···Oboryl hydrogen bond interactions, which are strengthened by bidentate C^C ligand introduction. The method shows broad substrate scope and high functional group tolerance. |
| first_indexed | 2024-03-08T18:42:08Z |
| format | Article |
| id | doaj.art-92c674ce413e4acfb7d0630ec3f18040 |
| institution | Directory Open Access Journal |
| issn | 2666-5549 |
| language | English |
| last_indexed | 2024-03-08T18:42:08Z |
| publishDate | 2023-11-01 |
| publisher | KeAi Communications Co. Ltd. |
| record_format | Article |
| series | Green Synthesis and Catalysis |
| spelling | doaj.art-92c674ce413e4acfb7d0630ec3f180402023-12-29T04:46:12ZengKeAi Communications Co. Ltd.Green Synthesis and Catalysis2666-55492023-11-0144300305Protecting-group-free ortho-C–H borylation of anilines enabled by mesoionic carbene-Ir complexZengyu Zhang0Shiqing Huang1Wei Liu2Liang-Liang Zhao3Chubin Hu4Xiaoyu Yan5Key Laboratory of Advanced Light Conversion Materials and Biophotonics, Department of Chemistry, Renmin University of China, Beijing 100872, ChinaKey Laboratory of Advanced Light Conversion Materials and Biophotonics, Department of Chemistry, Renmin University of China, Beijing 100872, ChinaKey Laboratory of Advanced Light Conversion Materials and Biophotonics, Department of Chemistry, Renmin University of China, Beijing 100872, ChinaKey Laboratory of Advanced Light Conversion Materials and Biophotonics, Department of Chemistry, Renmin University of China, Beijing 100872, ChinaKey Laboratory of Advanced Light Conversion Materials and Biophotonics, Department of Chemistry, Renmin University of China, Beijing 100872, ChinaCorresponding author.; Key Laboratory of Advanced Light Conversion Materials and Biophotonics, Department of Chemistry, Renmin University of China, Beijing 100872, ChinaWe describe an iridium-catalyzed ortho-selective C–H borylation of unprotected anilines. The employing strong σ-donating cyclometalated mesoionic carbene as C^C bidentate ligand is crucial for the high ortho-selectivity. Computational studies support outer-sphere X–H···Oboryl hydrogen bond interactions, which are strengthened by bidentate C^C ligand introduction. The method shows broad substrate scope and high functional group tolerance.http://www.sciencedirect.com/science/article/pii/S266655492200045XProtecting-group-freeC–H borylationHydrogen bondingRegioselectivityMesoionic carbene |
| spellingShingle | Zengyu Zhang Shiqing Huang Wei Liu Liang-Liang Zhao Chubin Hu Xiaoyu Yan Protecting-group-free ortho-C–H borylation of anilines enabled by mesoionic carbene-Ir complex Green Synthesis and Catalysis Protecting-group-free C–H borylation Hydrogen bonding Regioselectivity Mesoionic carbene |
| title | Protecting-group-free ortho-C–H borylation of anilines enabled by mesoionic carbene-Ir complex |
| title_full | Protecting-group-free ortho-C–H borylation of anilines enabled by mesoionic carbene-Ir complex |
| title_fullStr | Protecting-group-free ortho-C–H borylation of anilines enabled by mesoionic carbene-Ir complex |
| title_full_unstemmed | Protecting-group-free ortho-C–H borylation of anilines enabled by mesoionic carbene-Ir complex |
| title_short | Protecting-group-free ortho-C–H borylation of anilines enabled by mesoionic carbene-Ir complex |
| title_sort | protecting group free ortho c h borylation of anilines enabled by mesoionic carbene ir complex |
| topic | Protecting-group-free C–H borylation Hydrogen bonding Regioselectivity Mesoionic carbene |
| url | http://www.sciencedirect.com/science/article/pii/S266655492200045X |
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