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O-Glycosidation reactions promoted by in situ generated silver N-heterocyclic carbenes in ionic liquids

  1. Author:
    Talisman, I. J.
    Kumar, V.
    Razzaghy, J.
    Malhotra, S. V.

  2. Author Address

    [Talisman, IJ; Kumar, V; Razzaghy, J; Malhotra, SV] NCI, Lab Synthet Chem, SAIC Frederick Inc, Frederick, MD 21702 USA;Malhotra, SV (reprint author), NCI, Lab Synthet Chem, SAIC Frederick Inc, 1050 Boyles St, Frederick, MD 21702 USA;malhotrasa@mail.nih.gov
    1. Year: 2011
    2. Date: May
  2. Journal: Carbohydrate Research
    1. 346
    2. 7
    3. Pages: 883-890
  4. Type of Article: Article
  5. ISSN: 0008-6215
  1. Abstract:

    We herein report O-glycosidation reactions promoted via silver N-heterocyclic carbene complexes formed in situ in ionic liquids. Seven different room temperature ionic liquids were screened for the glycosidation reaction of 4-nitrophenol with tetra-O-acetyl-alpha-D-galactopyranosyl bromide. Good to excellent yields were obtained using Ag-NHC complexes derived from imidazolium halide salts to promote the glycosidation reaction, whereas yields considered moderate to low were obtained without use of the silver carbene complex. Anion metathesis of the ionic liquids with inexpensive alkylammonium halides also resulted in silver N-heterocyclic carbene formation and subsequent O-glycosidation in the presence of silver carbonate. Effective utility of this methodology has been demonstrated with biologically relevant acceptors (including flavones and steroids) where O-beta-glycoside products were obtained selectively in moderate to good yields. We have also demonstrated that the Ag-NHC complex is a superior promoter to traditionally used silver carbonate for the glycosidation of polyphenolic acceptors. The ionic liquids used in the study could be recycled three times without apparent loss in activity. (C) 2011 Published by Elsevier Ltd.

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External Sources

  1. View Full Text
  2. DOI: 10.1016/j.carres.2011.03.007
  3. View record in Web of Science®
  4. WOS: 000291176400001

Library Notes

  1. Fiscal Year: FY2010-2011
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