POTASSIUM TRIETHYLSILANOLATE, 95%

Product Code: SIP6899.0
CAS No: 25706-33-6
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25706-33-6
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Price
 
10 g
$100.00
50 g
$396.00

Product data and descriptions listed are typical values, not intended to be used as specification.

  • HMIS

    3-2-1-X
  • Molecular Formula

    C6H15KOSi
  • Molecular Weight (g/mol)

    170.37
  • Purity (%)

    95%
  • TSCA

    No
  • Boiling Point (˚C/mmHg)

    NA

Additional Properties

  • Hydrolytic Sensitivity

    7: reacts slowly with moisture/water

    • Application

    Used as a nucleophiles in the enantioselective formation of allyl alcohols from allyl carbonates.1
    Employed in an inexpensive vinylation of aryl bromides.2
    Catalyst for the cross-coupling of aryl and vinylsilanes.3

    Reference

    1. Lyothier, I. et al. Angew. Chem., Int. Ed. Engl. 2006, 45, 6204.
    2. Denmark, S. E.; Butler, C.R. J. Am. Chem. Soc. 2008, 130, 3690.
    3. Jeffery, T. Tetrahedron Lett. 1999, 40, 1673.

    Safety

  • Packaging Under

    Nitrogen

    • Silane Cross-Coupling Agent

    The cross-coupling reaction is a highly useful methodology for the formation of carbon-carbon bonds. It involves two reagents, with one typically being a suitable organometallic reagent - the nucleophile - and the other a suitable organic substrate, normally an unsaturated halide, tosylate or similar - the electrophile.

    Potassium triethylsilanolate; Potassium triethylsiloxide; Triethylsilanol, potassium salt

  • Soluble: methylene chloride, THF
  • Catalyst for the cross-coupling of aryl and vinylsilanes
  • Greater solubility and reactivity than KOSiMe3
  • Used as a nucleophiles in the enantioselective formation of allyl alcohols from allyl carbonates
  • Employed in an inexpensive vinylation of aryl bromides
  • Extensive review of silicon based cross-coupling agents: Denmark, S. E. et al. "Organic Reactions, Volume 75" Denmark, S. E. ed., John Wiley and Sons, 233, 2011

    • Silicon Chemistry, Articles

    Silicon-Based Formation of Carbon-Carbon Bonds – Larson

    Hatanaka and Hiyama first reported the palladium-catalyzed, fluoride-promoted reaction of aryl, alkenyl, allyl, and ethynyltrimethylsilanes with aryl, vinil and allyl halides to form the respective cross-coupled products