Rhodium‐Catalyzed Oxidative CH o‐Arylation of s‐Aryltetrazines with Aryl Boronic Acids: One‐Step Selective Access to T‐Shaped and Z‐Shaped Polyaromatics
Fuente:
Wiley Open Access
Gespeichert in:
| Hauptverfasser: | , , , , , , |
|---|---|
| Format: | Artículo Open Access |
| Veröffentlicht: |
Wiley
2025
|
| Schlagworte: | |
| Online-Zugang: | |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| _version_ | 1867021075154468864 |
|---|---|
| author | Oumaima Abidi Gaëlle Divoux Loris Gelin Hélène Cattey Paul Fleurat‐Lessard Jean‐Cyrille Hierso Julien Roger |
| author_facet | Oumaima Abidi Gaëlle Divoux Loris Gelin Hélène Cattey Paul Fleurat‐Lessard Jean‐Cyrille Hierso Julien Roger Oumaima Abidi Gaëlle Divoux Loris Gelin Hélène Cattey Paul Fleurat‐Lessard Jean‐Cyrille Hierso Julien Roger |
| collection | Wiley Open Access |
| contents | Rhodium‐Catalyzed Oxidative CH o‐Arylation of s‐Aryltetrazines with Aryl Boronic Acids: One‐Step Selective Access to T‐Shaped and Z‐Shaped Polyaromatics Oumaima Abidi Gaëlle Divoux Loris Gelin Hélène Cattey Paul Fleurat‐Lessard Jean‐Cyrille Hierso Julien Roger Advanced Synthesis & Catalysis The N‐directed rhodium‐catalyzed CH bond arylation of s‐aryltetrazine is reported using arylboronic acids as coupling partners. Convenient synthetic conditions are identified that avoid the 1,4‐azaphilic addition of the organometallic reagents on the tetrazine core, that may occur with organometallic nucleophiles, such as aryl cuprates. Thus, using [RhCl2Cp*]2 and Cu(OAc)2 in trifluoromethylbenzene favors the CH activation and direct arylation of the s‐tetrazine. This setup tolerates both electron‐donating and electron‐withdrawing groups on the (hetero)aryl boronic acids. Electron‐rich aryl coupling partners display a higher reactivity, and allow the formation of polyaromatic derivatives. This methodology provides a facile and straightforward route to diversely structured polyaromatics incorporating the valuable s‐tetrazine core, with so‐called T‐shaped and Z‐shaped architectures. 10.1002/adsc.70021 http://creativecommons.org/licenses/by-nc-nd/4.0/ |
| doi_str_mv | 10.1002/adsc.70021 |
| format | Artículo Open Access |
| id | wiley_oa_10_1002_adsc_70021 |
| institution | Wiley Open Access |
| license_str_mv | http://creativecommons.org/licenses/by-nc-nd/4.0/ |
| publishDate | 2025 |
| publisher | Wiley |
| record_format | wiley_oa |
| spellingShingle | Rhodium‐Catalyzed Oxidative CH o‐Arylation of s‐Aryltetrazines with Aryl Boronic Acids: One‐Step Selective Access to T‐Shaped and Z‐Shaped Polyaromatics Oumaima Abidi Gaëlle Divoux Loris Gelin Hélène Cattey Paul Fleurat‐Lessard Jean‐Cyrille Hierso Julien Roger Advanced Synthesis & Catalysis Rhodium‐Catalyzed Oxidative CH o‐Arylation of s‐Aryltetrazines with Aryl Boronic Acids: One‐Step Selective Access to T‐Shaped and Z‐Shaped Polyaromatics Oumaima Abidi Gaëlle Divoux Loris Gelin Hélène Cattey Paul Fleurat‐Lessard Jean‐Cyrille Hierso Julien Roger Advanced Synthesis & Catalysis The N‐directed rhodium‐catalyzed CH bond arylation of s‐aryltetrazine is reported using arylboronic acids as coupling partners. Convenient synthetic conditions are identified that avoid the 1,4‐azaphilic addition of the organometallic reagents on the tetrazine core, that may occur with organometallic nucleophiles, such as aryl cuprates. Thus, using [RhCl2Cp*]2 and Cu(OAc)2 in trifluoromethylbenzene favors the CH activation and direct arylation of the s‐tetrazine. This setup tolerates both electron‐donating and electron‐withdrawing groups on the (hetero)aryl boronic acids. Electron‐rich aryl coupling partners display a higher reactivity, and allow the formation of polyaromatic derivatives. This methodology provides a facile and straightforward route to diversely structured polyaromatics incorporating the valuable s‐tetrazine core, with so‐called T‐shaped and Z‐shaped architectures. 10.1002/adsc.70021 http://creativecommons.org/licenses/by-nc-nd/4.0/ |
| title | Rhodium‐Catalyzed Oxidative CH o‐Arylation of s‐Aryltetrazines with Aryl Boronic Acids: One‐Step Selective Access to T‐Shaped and Z‐Shaped Polyaromatics |
| topic | Advanced Synthesis & Catalysis |
| url | https://advanced.onlinelibrary.wiley.com/doi/10.1002/adsc.70021 |