| Publikationstyp: | Beitrag in wissenschaftlicher Zeitschrift |
| Art der Begutachtung: | Peer review (Publikation) |
| Titel: | Negishi cross-coupling reactions catalyzed by an aminophosphine-based nickel system : a reliable and general applicable reaction protocol for the high-yielding synthesis of biaryls |
| Autor/-in: | Gerber, Roman Frech, Christian M. |
| DOI: | 10.1002/chem.201101037 |
| Erschienen in: | Chemistry - A European Journal |
| Band(Heft): | 17 |
| Heft: | 42 |
| Seite(n): | 11893 |
| Seiten bis: | 11904 |
| Erscheinungsdatum: | 2011 |
| Verlag / Hrsg. Institution: | Wiley |
| ISSN: | 0947-6539 1521-3765 |
| Sprache: | Englisch |
| Fachgebiet (DDC): | 540: Chemie |
| Zusammenfassung: | Treatment of NMP solutions of NiCl(2) with 1,1',1''-(phosphanetriyl)tripiperidine (≈2.05 equiv), dissolved in THF, in air at 25°C forms a highly active catalytic system for the cross-coupling of a large variety of electronically activated, non-activated, deactivated, and ortho-substituted, heterocyclic, and functionalized aryl bromides and aryl chlorides with diarylzinc reagents. Very high levels of conversion and yields were obtained within 2 h at 60°C in the presence of only 0.1 mol% of catalyst (based on nickel) and thus at catalyst loadings far lower than typically reported for nickel-catalyzed versions of the Negishi reaction. Various aryl halides-which may contain trifluoromethyl groups, fluorides, or other functional groups such as acetals, ketones, ethers, esters, lactones, amides, imines, anilines, alkenes, pyridines, quinolines, and pyrimidines-were successfully converted into the corresponding biaryls. Electronic and steric variations are tolerated in both reaction partners. Experimental observations indicate that a molecular (Ni(I)/Ni(III)) mechanism is operative. |
| URI: | https://digitalcollection.zhaw.ch/handle/11475/9850 |
| Volltext Version: | Publizierte Version |
| Lizenz (gemäss Verlagsvertrag): | Lizenz gemäss Verlagsvertrag |
| Departement: | Life Sciences und Facility Management |
| Enthalten in den Sammlungen: | Publikationen Life Sciences und Facility Management |
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Gerber, R., & Frech, C. M. (2011). Negishi cross-coupling reactions catalyzed by an aminophosphine-based nickel system : a reliable and general applicable reaction protocol for the high-yielding synthesis of biaryls. Chemistry - A European Journal, 17(42), 11893–11904. https://doi.org/10.1002/chem.201101037
Gerber, R. and Frech, C.M. (2011) ‘Negishi cross-coupling reactions catalyzed by an aminophosphine-based nickel system : a reliable and general applicable reaction protocol for the high-yielding synthesis of biaryls’, Chemistry - A European Journal, 17(42), pp. 11893–11904. Available at: https://doi.org/10.1002/chem.201101037.
R. Gerber and C. M. Frech, “Negishi cross-coupling reactions catalyzed by an aminophosphine-based nickel system : a reliable and general applicable reaction protocol for the high-yielding synthesis of biaryls,” Chemistry - A European Journal, vol. 17, no. 42, pp. 11893–11904, 2011, doi: 10.1002/chem.201101037.
GERBER, Roman und Christian M. FRECH, 2011. Negishi cross-coupling reactions catalyzed by an aminophosphine-based nickel system : a reliable and general applicable reaction protocol for the high-yielding synthesis of biaryls. Chemistry - A European Journal. 2011. Bd. 17, Nr. 42, S. 11893–11904. DOI 10.1002/chem.201101037
Gerber, Roman, and Christian M. Frech. 2011. “Negishi Cross-Coupling Reactions Catalyzed by an Aminophosphine-Based Nickel System : A Reliable and General Applicable Reaction Protocol for the High-Yielding Synthesis of Biaryls.” Chemistry - A European Journal 17 (42): 11893–904. https://doi.org/10.1002/chem.201101037.
Gerber, Roman, and Christian M. Frech. “Negishi Cross-Coupling Reactions Catalyzed by an Aminophosphine-Based Nickel System : A Reliable and General Applicable Reaction Protocol for the High-Yielding Synthesis of Biaryls.” Chemistry - A European Journal, vol. 17, no. 42, 2011, pp. 11893–904, https://doi.org/10.1002/chem.201101037.
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