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
Please wait while Download options loads

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

Search articles by author