π‐Extended Pleiadienes by [5+2] Annulation of 1‐Boraphenalenes and ortho‐Dihaloarenes
Please always quote using this URN: urn:nbn:de:bvb:20-opus-293919
- 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.…
Author: | Matthias Schnitzlein, Chongwei Zhu, Kazutaka Shoyama, Frank WürthnerORCiDGND |
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URN: | urn:nbn:de:bvb:20-opus-293919 |
Document Type: | Journal article |
Faculties: | Fakultät für Chemie und Pharmazie / Institut für Organische Chemie |
Language: | English |
Parent Title (English): | Chemistry – A European Journal |
Year of Completion: | 2022 |
Volume: | 28 |
Issue: | 61 |
Article Number: | e202202053 |
Source: | Chemistry – A European Journal 2022, 28(61):e202202053. DOI: 10.1002/chem.202202053 |
DOI: | https://doi.org/10.1002/chem.202202053 |
Dewey Decimal Classification: | 5 Naturwissenschaften und Mathematik / 54 Chemie / 540 Chemie und zugeordnete Wissenschaften |
Tag: | annulation; aromaticity; azulene; cyclodehydrogenation; polycyclic aromatic hydrocarbons |
Release Date: | 2023/06/19 |
Licence (German): | CC BY: Creative-Commons-Lizenz: Namensnennung 4.0 International |