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Synthesis of fulvene vinyl ethers by gold catalysis

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-c...

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Hauptverfasser: Ahrens, Alexander (VerfasserIn) , Schwarz, Julia (VerfasserIn) , Lustosa, Danilo Machado (VerfasserIn) , Pourkaveh, Raheleh (VerfasserIn) , Hoffmann, Marvin (VerfasserIn) , Rominger, Frank (VerfasserIn) , Rudolph, Matthias (VerfasserIn) , Dreuw, Andreas (VerfasserIn) , Hashmi, A. Stephen K. (VerfasserIn)
Dokumenttyp: Article (Journal)
Sprache:Englisch
Veröffentlicht: April 6, 2020
In: Chemistry - a European journal
Year: 2020, Jahrgang: 26, Heft: 23, Pages: 5280-5287
ISSN:1521-3765
DOI:10.1002/chem.202000338
Online-Zugang:Verlag, kostenfrei, Volltext: https://doi.org/10.1002/chem.202000338
Verlag, kostenfrei, Volltext: https://chemistry-europe.onlinelibrary.wiley.com/doi/full/10.1002/chem.202000338
Volltext
Verfasserangaben:Alexander Ahrens, Julia Schwarz, Danilo M. Lustosa, Raheleh Pourkaveh, Marvin Hoffmann, Frank Rominger, Matthias Rudolph, Andreas Dreuw, and A. Stephen K. Hashmi
Beschreibung
Zusammenfassung: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.
Beschreibung:Gesehen am 12.05.2020
Beschreibung:Online Resource
ISSN:1521-3765
DOI:10.1002/chem.202000338

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