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Synthesis of fulvene vinyl ethers by gold catalysis

Ahrens, A ; Sharif University of Technology | 2020

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  1. Type of Document: Article
  2. DOI: 10.1002/chem.202000338
  3. Publisher: Wiley-VCH Verlag , 2020
  4. Abstract:
  5. 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. © 2020 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA
  6. Keywords:
  7. Aryl cations ; Fulvene ethers ; Gold catalysis ; Vinyl cations ; Catalysis ; Chlorine compounds ; Ethers ; Fluorine compounds ; Gold ; Ketones ; Regioselectivity ; Scaffolds ; Thermoanalysis ; Aryl fluorides ; Controlled switching ; Cyclizations ; Fulvenes ; Gold catalysis ; Thermo dynamic analysis ; Unknown class ; Vinyl ethers ; Cyclization
  8. Source: Chemistry - A European Journal ; Volume 26, Issue 23 , 2020 , Pages 5280-5287
  9. URL: https://chemistry-europe.onlinelibrary.wiley.com/doi/full/10.1002/chem.202000338