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| Verfasst von: | Ahrens, Alexander [VerfasserIn]  |
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| | Schwarz, Julia [VerfasserIn] |
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| | Lustosa, Danilo Machado [VerfasserIn] |
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| | Pourkaveh, Raheleh [VerfasserIn] |
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| | Hoffmann, Marvin [VerfasserIn] |
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| | Rominger, Frank [VerfasserIn] |
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| | Rudolph, Matthias [VerfasserIn] |
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| | Dreuw, Andreas [VerfasserIn] |
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| | Hashmi, A. Stephen K. [VerfasserIn] |
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| Titel: | Synthesis of fulvene vinyl ethers by gold catalysis |
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| Verf.angabe: | Alexander Ahrens, Julia Schwarz, Danilo M. Lustosa, Raheleh Pourkaveh, Marvin Hoffmann, Frank Rominger, Matthias Rudolph, Andreas Dreuw, and A. Stephen K. Hashmi |
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| E-Jahr: | 2020 |
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| Jahr: | April 6, 2020 |
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| Umfang: | 8 S. |
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| Fussnoten: | Gesehen am 12.05.2020 |
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| Titel Quelle: | Enthalten in: Chemistry - a European journal |
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| Ort Quelle: | Weinheim : Wiley-VCH, 1995 |
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| Jahr Quelle: | 2020 |
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| Band/Heft Quelle: | 26(2020), 23, Seite 5280-5287 |
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| ISSN Quelle: | 1521-3765 |
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| Abstract: | Abstract Gold-catalyzed cyclization of 1,5-diynes with ketones as reagents and solvent provides diversely substituted vinyl ethers under mild conditions. The regioselectivity of such gold-catalyzed cyclizations is usually controlled by the scaffold of the diyne. Herein, we report the first solvent-controlled switching of regioselectivity from a 6-endo-dig- to 5-endo-dig-cyclization in these transformations, providing fulvene derivatives. With respect to the functional-group tolerance, aryl fluorides, chlorides, bromides, and ethers are tolerated. Furthermore, the mechanism and selectivity are put to scrutiny by experimental studies and a thermodynamic analysis of the product. Additionally, 6-(vinyloxy)fulvenes are a hitherto unknown class of compounds. Their reactivity is briefly evaluated, to give insights into their potential applications. |
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| DOI: | doi:10.1002/chem.202000338 |
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| URL: | kostenfrei: Volltext ; Verlag: https://doi.org/10.1002/chem.202000338 |
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| | kostenfrei: Volltext: https://chemistry-europe.onlinelibrary.wiley.com/doi/full/10.1002/chem.202000338 |
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| | DOI: https://doi.org/10.1002/chem.202000338 |
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| Datenträger: | Online-Ressource |
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| Sprache: | eng |
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| Sach-SW: | aryl cations |
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| | fulvene ethers |
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| | gold catalysis |
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| | vinyl cations |
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| | vinyl ethers |
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| K10plus-PPN: | 1698010761 |
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| Verknüpfungen: | → Zeitschrift |
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| Lokale URL UB: |  Zum Volltext |
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Synthesis of fulvene vinyl ethers by gold catalysis / Ahrens, Alexander [VerfasserIn]; April 6, 2020 (Online-Ressource)
