| Publikationstyp: | Beitrag in wissenschaftlicher Zeitschrift |
| Art der Begutachtung: | Peer review (Publikation) |
| Titel: | Transition metal-free amination of aryl halides : a simple and reliable method for the efficient and high-yielding synthesis of N-arylated amines |
| Autor/-in: | Bolliger, Jeanne L. Frech, Christian M. |
| DOI: | 10.1016/j.tet.2008.11.072 |
| Erschienen in: | Tetrahedron |
| Band(Heft): | 65 |
| Heft: | 6 |
| Seite(n): | 1180 |
| Seiten bis: | 1187 |
| Erscheinungsdatum: | 2009 |
| Verlag / Hrsg. Institution: | Elsevier |
| ISSN: | 0040-4020 1464-5416 |
| Sprache: | Englisch |
| Fachgebiet (DDC): | 540: Chemie |
| Zusammenfassung: | A simple and reliable reaction protocol for the clean, fast, and high-yielding synthesis of various N-arylated amines derived from reactions of aryl halides with various (also sterically hindered) amines under transition metal-free reaction conditions is presented. Dioxane and KN(Si(CH3)3)2 were found to be the ideal solvent and base for this transformation. The conversion rates and yields observed are excellent and in the majority of the reactions performed significantly higher than that obtained in their catalyzed versions. Furthermore, the selective synthesis of 6-halopyridin-2-amines and asymmetric pyridine-2,6-diamines (derived from consecutive reactions of 2,6-dibromopyridine and 2,6-dichloropyridine, respectively, with different amines) is possible in almost quantitative yields (relative to 2,6-dihalopyridine) within very short reaction times. Purification of the 6-halopyridin-2-amine intermediates is not necessary, allowing the synthesis of pyridine-2,6-diamines in ‘one-pot’. However, catalysts are in many cases not required to efficiently and selectively couple aryl halides with amines, making transition metal-free versions of the Buchwald–Hartwig reaction extremely attractive for the synthesis of N-arylated amines with substrates containing substituents on the aryl halide, which either promote regioselectivity and/or do not require regioselective aminations. |
| URI: | https://digitalcollection.zhaw.ch/handle/11475/10483 |
| 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 |
Dateien zu dieser Ressource:
Es gibt keine Dateien zu dieser Ressource.
Zur Langanzeige
Bolliger, J. L., & Frech, C. M. (2009). Transition metal-free amination of aryl halides : a simple and reliable method for the efficient and high-yielding synthesis of N-arylated amines. Tetrahedron, 65(6), 1180–1187. https://doi.org/10.1016/j.tet.2008.11.072
Bolliger, J.L. and Frech, C.M. (2009) ‘Transition metal-free amination of aryl halides : a simple and reliable method for the efficient and high-yielding synthesis of N-arylated amines’, Tetrahedron, 65(6), pp. 1180–1187. Available at: https://doi.org/10.1016/j.tet.2008.11.072.
J. L. Bolliger and C. M. Frech, “Transition metal-free amination of aryl halides : a simple and reliable method for the efficient and high-yielding synthesis of N-arylated amines,” Tetrahedron, vol. 65, no. 6, pp. 1180–1187, 2009, doi: 10.1016/j.tet.2008.11.072.
BOLLIGER, Jeanne L. und Christian M. FRECH, 2009. Transition metal-free amination of aryl halides : a simple and reliable method for the efficient and high-yielding synthesis of N-arylated amines. Tetrahedron. 2009. Bd. 65, Nr. 6, S. 1180–1187. DOI 10.1016/j.tet.2008.11.072
Bolliger, Jeanne L., and Christian M. Frech. 2009. “Transition Metal-Free Amination of Aryl Halides : A Simple and Reliable Method for the Efficient and High-Yielding Synthesis of N-Arylated Amines.” Tetrahedron 65 (6): 1180–87. https://doi.org/10.1016/j.tet.2008.11.072.
Bolliger, Jeanne L., and Christian M. Frech. “Transition Metal-Free Amination of Aryl Halides : A Simple and Reliable Method for the Efficient and High-Yielding Synthesis of N-Arylated Amines.” Tetrahedron, vol. 65, no. 6, 2009, pp. 1180–87, https://doi.org/10.1016/j.tet.2008.11.072.
Alle Ressourcen in diesem Repository sind urheberrechtlich geschützt, soweit nicht anderweitig angezeigt.