Controlling Regioselectivity in Palladium‐Catalyzed C−H Activation/Aryl–Aryl Coupling of 4‐Phenylamino (2.2) paracyclophane
Abstract: Selective activation/functionalization of C−H bonds has emerged as an atom‐ and step‐economical process at the forefront of modern synthetic chemistry. This work reports palladium‐catalyzed exclusively para‐selective C−H activation/aryl–aryl bond formation with a preference over N‐arylation under the Buchwald–Hartwig amination reaction of 4‐phenylamino[2.2]paracyclophane. This innovative synthetic strategy allows a facile preparation of [2.2]paracyclophane derivatives featuring disparate para‐substitutions at C‐4 and C‐7 positions in a highly selective manner, gives access to a series of potential candidates for [2.2]paracyclophane‐derived new planar chiral ligands. The unprecedented behavior in reactivity and preferential selectivity of C−C coupling over C−N bond formation via C−H activation is unique to the [2.2]paracyclophane scaffold compared to the non‐cyclophane analogue under the same reaction conditions. Selective C−H activation/aryl–aryl bond formation and sequential C−N coupling product formation is evidenced unambiguously by X‐ray crystallography.
- Standort
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Deutsche Nationalbibliothek Frankfurt am Main
- Umfang
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Online-Ressource
- Sprache
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Englisch
- Erschienen in
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Controlling Regioselectivity in Palladium‐Catalyzed C−H Activation/Aryl–Aryl Coupling of 4‐Phenylamino (2.2) paracyclophane ; volume:26 ; number:61 ; year:2020 ; pages:13771-13775 ; extent:5
Chemistry - a European journal ; 26, Heft 61 (2020), 13771-13775 (gesamt 5)
- Urheber
- DOI
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10.1002/chem.202003709
- URN
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urn:nbn:de:101:1-2022060513484771858229
- Rechteinformation
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Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
- Letzte Aktualisierung
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15.08.2025, 07:22 MESZ
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Beteiligte
- Zippel, Christoph
- Spuling, Eduard
- Hassan, Zahid
- Polamo, Mika
- Nieger, Martin
- Bräse, Stefan
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