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dc.contributor.authorBolliger, Jeanne L.-
dc.contributor.authorFrech, Christian M.-
dc.date.accessioned2018-09-12T14:07:34Z-
dc.date.available2018-09-12T14:07:34Z-
dc.date.issued2009-
dc.identifier.issn0040-4020de_CH
dc.identifier.issn1464-5416de_CH
dc.identifier.urihttps://digitalcollection.zhaw.ch/handle/11475/10483-
dc.description.abstractA 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.de_CH
dc.language.isoende_CH
dc.publisherElsevierde_CH
dc.relation.ispartofTetrahedronde_CH
dc.rightsLicence according to publishing contractde_CH
dc.subject.ddc540: Chemiede_CH
dc.titleTransition metal-free amination of aryl halides : a simple and reliable method for the efficient and high-yielding synthesis of N-arylated aminesde_CH
dc.typeBeitrag in wissenschaftlicher Zeitschriftde_CH
dcterms.typeTextde_CH
zhaw.departementLife Sciences und Facility Managementde_CH
dc.identifier.doi10.1016/j.tet.2008.11.072de_CH
zhaw.funding.euNode_CH
zhaw.issue6de_CH
zhaw.originated.zhawNode_CH
zhaw.pages.end1187de_CH
zhaw.pages.start1180de_CH
zhaw.publication.statuspublishedVersionde_CH
zhaw.volume65de_CH
zhaw.publication.reviewPeer review (Publikation)de_CH
Appears in collections:Publikationen Life Sciences und Facility Management

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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.


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