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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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Main Authors: Ahrens, Alexander (Author) , Schwarz, Julia (Author) , Lustosa, Danilo Machado (Author) , Pourkaveh, Raheleh (Author) , Hoffmann, Marvin (Author) , Rominger, Frank (Author) , Rudolph, Matthias (Author) , Dreuw, Andreas (Author) , Hashmi, A. Stephen K. (Author)
Format: Article (Journal)
Language:English
Published: April 6, 2020
In: Chemistry - a European journal
Year: 2020, Volume: 26, Issue: 23, Pages: 5280-5287
ISSN:1521-3765
DOI:10.1002/chem.202000338
Online Access: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
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Author Notes: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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Summary: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.
Item Description:Gesehen am 12.05.2020
Physical Description:Online Resource
ISSN:1521-3765
DOI:10.1002/chem.202000338

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