Zinc triflate

Zinc triflate
Names
IUPAC name
zinc trifluoromethanesulfonate
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.053.548 Edit this at Wikidata
  • InChI=1S/2CHF3O3S.Zn/c2*2-1(3,4)8(5,6)7;/h2*(H,5,6,7);/q;;+2/p-2 checkY
    Key: CITILBVTAYEWKR-UHFFFAOYSA-L checkY
  • InChI=1/2CHF3O3S.Zn/c2*2-1(3,4)8(5,6)7;/h2*(H,5,6,7);/q;;+2/p-2
    Key: CITILBVTAYEWKR-NUQVWONBAZ
  • [Zn+2].FC(F)(F)S([O-])(=O)=O.FC(F)(F)S([O-])(=O)=O
Properties
C2F6O6S2Zn
Molar mass 363.51 g·mol−1
Appearance White powder
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Zinc trifluoromethanesulfonate or zinc triflate is the zinc salt of trifluoromethanesulfonic acid. It is commonly used as a Lewis acid catalyst, e.g. in silylations.[1]

A white powder, zinc triflate is commercially available, though some workers have experienced inconsistent results with zinc triflate from different sources.[2][3] If desired, it may be prepared from reacting trifluoromethanesulfonic acid with zinc metal in acetonitrile,[4] or with zinc carbonate in methanol:[5]

Zn + 2 HOTf → Zn(OTf)2 + H2
ZnCO3 + 2 HOTf → Zn(OTf)2 + H2O + CO2 (OTf = CF3SO3)

References

  1. ^ H. Jiang & S. Zhu (2005). "Silylation of 1-alkynes with chlorosilanes promoted by Zn(OTf)2: an efficient way to the preparation of alkynylsilanes". Tetrahedron Letters. 46 (3): 517–519. doi:10.1016/j.tetlet.2004.10.175.
  2. ^ R. J. Rahaim & J. T. Shaw (2008). "Zinc-Catalyzed Silylation of Terminal Alkynes". J. Org. Chem. 73 (7): 2912–2915. doi:10.1021/jo702557d. PMID 18331056.
  3. ^ J. E. D. Kirkham, T. D. L. Courtney, V. Lee and J. E. Baldwin (2005). "Asymmetric synthesis of cytotoxic sponge metabolites R-strongylodiols A and B and an analogue". Tetrahedron. 61 (30): 7219–7232. doi:10.1016/j.tet.2005.05.034.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  4. ^ J. Lombard, S. Romain, S. Dumas, J. Chauvin, M.-N. Collomb, D. Daveloose, A. Deronzier and J.-C. Leprêtre (2005). "Tetranuclear Polypyridyl Complexes of RuII and FeII: Synthesis, Electrochemical, Photophysical and Photochemical Behaviour". European Journal of Inorganic Chemistry. 2005 (16): 3320–3330. doi:10.1002/ejic.200500106.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  5. ^ E. J. Corey & K. Shimoji (1983). "Magnesium and zinc-catalyzed thioketalization". Tetrahedron Letters. 24 (2): 169–172. doi:10.1016/S0040-4039(00)81357-X.