Synlett 2010(1): 161-162  
DOI: 10.1055/s-0029-1218515
SPOTLIGHT
© Georg Thieme Verlag Stuttgart ˙ New York

Ytterbium Triflate: A Green Catalyst

Carina I. C. Crucho
REQUIMTE, Departamento de Química, Faculdade de Ciências e Tecnologia, Universidade Nova de Lisboa, 2829-516 Caparica, Portugal.
e-Mail: carinacrucho@gmail.com;
Further Information

Publication History

Publication Date:
14 December 2009 (online)

Introduction

Ytterbium triflate (1) is known to be a useful mild, versatile, and environmentally friendly Lewis acid catalyst. With the ever-increasing interest in the sustainable development, Yb(OTf)3 benefits from its characteristic features: High efficiency in green media, such as water and ionic liquids, recovery after reaction completion, and reusing without loss of activity. [¹] Contrary to other Lewis acids, Yb(OTf)3 is effectively used in catalytic amounts and is widely employed in organic synthesis promoting several carbon-carbon and carbon-heteroatom bond formation, which include the aldol condensations, Mannich-type reaction, Diels-Alder cycloadditions, Friedel-Crafts acylation or alkylation, and heterocycle synthesis. [¹] Moreover, taking its advantage of the affinity to nitrogen-­containing compounds, which deactivate most Lewis ­acids, Yb(OTf)3 enhances the reactivity of the imine group and catalyses an imine ene reaction providing useful homo­allylic amines, [²] and also increases the yield of the Ugi four-component coupling. [³]

    References

  • 1 Kobayashi S. Sugiura M. Kitagawa H. Lam WW.-L. Chem. Rev.  2002,  102:  2227 
  • 2 Yamanaka M. Nishida A. Nakagawa M. J. Org. Chem.  2003,  68:  3112 
  • 3 Okandeji BO. Gordon JR. Sello JK. J. Org. Chem.  2008,  73:  5595 
  • 4 Fukuzumi S. Satoh N. Okamoto T. Yasui K. Suenobu T. Seko Y. Fujitsuka M. Ito O. J. Am. Chem. Soc.  2001,  123:  7756 
  • 5 Huang Y.-J. Yang F.-Y. Zhu C.-J. J. Am. Chem. Soc.  2005,  127:  16386 
  • 6 Yu C.-M. Dai X.-P. Su W.-K. Synlett  2007,  646 
  • 7 Curini M. Epifano F. Genovese S. Marcotullio MC. Rosati O. Org. Lett.  2005,  7:  1331 
  • 8 Manabe K. Nobutou D. Kobayashi S. Bioorg. Med. Chem.  2005,  13:  5154 
  • 9 Mudiganti NVS. Claessens S. De Kimpe N. Tetrahedron  2009,  65:  1716 
  • 10 Habaue S. Temma T. Sugiyama Y. Yan P. Tetrahedron Lett.  2007,  48:  8595 
  • 11 Turhan K. Pelit E. Turgut Z. Synth. Commun.  2009,  39:  1729