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: | , , , , , , , , |
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| Format: | Article (Journal) |
| Language: | English |
| Published: |
April 6, 2020
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| 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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| 520 | |a 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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