π‐Extended Pleiadienes by [5+2] Annulation of 1‐Boraphenalenes and ortho‐Dihaloarenes
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- Palladium‐catalyzed [5+2] annulation of 1‐boraphenalenes with ortho‐dihaloarenes afforded negatively curved π‐extended pleiadienes. Two benzo[1,2‐i:4,5‐i’]dipleiadienes (BDPs) featuring a seven‐six‐seven‐membered ring arrangement were synthesized and investigated. Their crystal structure revealed a unique packing arrangement and theoretical calculations were employed to shed light onto the dynamic behavior of the BDP moiety and its aromaticity. Further, a naphthalene‐fused pleiadiene was stitched together by oxidative cyclodehydrogenation toPalladium‐catalyzed [5+2] annulation of 1‐boraphenalenes with ortho‐dihaloarenes afforded negatively curved π‐extended pleiadienes. Two benzo[1,2‐i:4,5‐i’]dipleiadienes (BDPs) featuring a seven‐six‐seven‐membered ring arrangement were synthesized and investigated. Their crystal structure revealed a unique packing arrangement and theoretical calculations were employed to shed light onto the dynamic behavior of the BDP moiety and its aromaticity. Further, a naphthalene‐fused pleiadiene was stitched together by oxidative cyclodehydrogenation to yield an additional five‐membered ring. This formal azulene moiety led to distinct changes in optical and redox properties and increased perturbation of the aromatic system.…
Autor(en): | Matthias Schnitzlein, Chongwei Zhu, Kazutaka Shoyama, Frank WürthnerORCiDGND |
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URN: | urn:nbn:de:bvb:20-opus-293919 |
Dokumentart: | Artikel / Aufsatz in einer Zeitschrift |
Institute der Universität: | Fakultät für Chemie und Pharmazie / Institut für Organische Chemie |
Sprache der Veröffentlichung: | Englisch |
Titel des übergeordneten Werkes / der Zeitschrift (Englisch): | Chemistry – A European Journal |
Erscheinungsjahr: | 2022 |
Band / Jahrgang: | 28 |
Heft / Ausgabe: | 61 |
Aufsatznummer: | e202202053 |
Originalveröffentlichung / Quelle: | Chemistry – A European Journal 2022, 28(61):e202202053. DOI: 10.1002/chem.202202053 |
DOI: | https://doi.org/10.1002/chem.202202053 |
Allgemeine fachliche Zuordnung (DDC-Klassifikation): | 5 Naturwissenschaften und Mathematik / 54 Chemie / 540 Chemie und zugeordnete Wissenschaften |
Freie Schlagwort(e): | annulation; aromaticity; azulene; cyclodehydrogenation; polycyclic aromatic hydrocarbons |
Datum der Freischaltung: | 19.06.2023 |
Lizenz (Deutsch): | CC BY: Creative-Commons-Lizenz: Namensnennung 4.0 International |