261717-41-3

All structures are computer generated. Please rely on the product data below for placing your order. If you see any errors in structures, please email customer service so that they can be addressed.

(E)-HEPTENYLDIISOPROPYLSILANOL

Product Code: SIH5844.5

Cas No: 261717-41-3

2.5 g
$379.00
Save for Later
Alkenylsilane 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.

(E)-Heptenyldiisopropylsilanol; Hydroxydiisopropylheptenylsilane
  • Stable silanol for cross-coupling of olefinic group
  • Vinylsilanols couple w/ aryl triflates and nonflates
  • Undergoes Pd-catalyzed cross-coupling with activated aromatic iodides
  • Used for cross-coupling vinylations
  • Vinyl silanols cross-couple w/ aryl triflates and nonaflates
  • Potassium salts of silanols cross-couple in absence of fluoride
  • 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

    • Specific Gravity: 0.877

    HMIS Key: 2-2-0-X

    Hydrolytic Sensitivity: 4: no reaction with water under neutral conditions

    Formula: C13H28OSi

    Refractive Index: 1.4640

    Application: Undergoes Pd-catalyzed cross-coupling with activated aromatic iodides.1
    Stable silanol for cross-coupling vinylations.2,3,4
    Vinyl silanols cross-couple w/ aryl triflates and nonaflates.5
    Potassium salts of silanols cross-couple in absence of fluoride.6

    Reference: 1. Denmark, S. et al. Org. Syn. 2005, 81, 42.
    2. Denmark, S. E.; Sweis, R. F. J. Am. Chem. Soc. 2001, 123, 6439.
    3. Denmark, S. E.; Pan, W. J. Organomet. Chem. 2002, 653, 98.
    4. Denmark, S. E.; Wehrli, D. Org. Lett. 2000, 2, 565.
    5. Denmark, S. E.; Sweis, R. F. Org. Lett. 2002, 4, 3771.
    6. Denmark, S. E.; Kallemeyn, J. M. J. Am. Chem. Soc. 2006, 128, 15958.

    Fieser: