Jump to main content
Jump to site search

Issue 11, 2016
Previous Article Next Article

Gold-catalyzed cycloisomerization of trifluoromethylated allenols: sustainability and mechanistic studies

Author affiliations

Abstract

Trifluoromethyl-substituted α-allenols are cyclized to the corresponding 2,5-dihydrofurans in the presence of neutral or cationic gold catalysts. The catalyst can be recycled if ionic liquids (in particular [BMIM][PF6]) are used as reaction medium. The allene forms droplets in the ionic liquid generating a heterogeneous two-phasic system. Kinetic studies in organic solvents using electronically different gold catalysts allowed to identify the protodeauration of a σ-gold-species as rate-determining step of typical allene cyclizations. Only if a CF3 group is present at C-5, π-complex formation is rate-limiting.

Graphical abstract: Gold-catalyzed cycloisomerization of trifluoromethylated allenols: sustainability and mechanistic studies

Back to tab navigation

Supplementary files

Publication details

The article was received on 01 Aug 2016, accepted on 08 Sep 2016 and first published on 10 Sep 2016


Article type: Research Article
DOI: 10.1039/C6QO00423G
Citation: Org. Chem. Front., 2016,3, 1514-1519
  • Open access: Creative Commons BY-NC license
  •   Request permissions

    Gold-catalyzed cycloisomerization of trifluoromethylated allenols: sustainability and mechanistic studies

    L. Lempke, H. Sak, M. Kubicki and N. Krause, Org. Chem. Front., 2016, 3, 1514
    DOI: 10.1039/C6QO00423G

    This article is licensed under a Creative Commons Attribution-NonCommercial 3.0 Unported Licence. Material from this article can be used in other publications provided that the correct acknowledgement is given with the reproduced material and it is not used for commercial purposes.

    Reproduced material should be attributed as follows:

    • For reproduction of material from NJC:
      [Original citation] - Published by The Royal Society of Chemistry (RSC) on behalf of the Centre National de la Recherche Scientifique (CNRS) and the RSC.
    • For reproduction of material from PCCP:
      [Original citation] - Published by the PCCP Owner Societies.
    • For reproduction of material from PPS:
      [Original citation] - Published by The Royal Society of Chemistry (RSC) on behalf of the European Society for Photobiology, the European Photochemistry Association, and RSC.
    • For reproduction of material from all other RSC journals:
      [Original citation] - Published by The Royal Society of Chemistry.

    Information about reproducing material from RSC articles with different licences is available on our Permission Requests page.

Search articles by author

Spotlight

Advertisements