Description
Additional Properties
Hydrolytic Sensitivity 4: no reaction with water under neutral conditions Application Review of synthetic utility.1 Reacts w/ aryl aldehydes to form diethynylmethane derivatives.10 Useful in the preparation of unsymmetrical diarylacetylenes.11 Ethynylates aromatic compounds.2 Precursor to trimethylsilylethyny
l copper reagent.3 Lithiated derivative (n-BuLi treatment) reacts with halotriazines to produce monomers.4 Employed in ortho ethenylation of phenols.5 Undergoes Diels-Alder reactions with butadienes.6 Converts imines to propargyl amines.7 Forms propargylic amines from aldehydes and amines in aqueous system.8 Regioselectively forms either regioisomeric enyne upon addition to propargyl amines depending on catalyst employed.9 Reference 1. Handbook of Reagents for Organic Synthesis, Reagents for Silicon-Mediated Organic Synthesis, Fuchs, P. L. Ed., John Wiley and Sons, Ltd., 2011, p. 569-580. 10. Girard, D. et al. Tetrahedron Lett. 2007, 48, 6022. 11. Mio, M. et al. Org. Lett. 2002, 4, 3199. 2. Austin, W. et al. J. Org. Chem. 1981, 46, 2280. 3. Sakata, H. et al. Tetrahedron Lett. 1987, 28, 5719. 4. Kouveetakis, J. et al. Chem. Mater. 1994, 6, 636. 5. Kobayashi, K.; Yamaguchi, M. Org. Lett. 2001, 3, 241. 6. Paik, S.-J. et al. Org. Lett. 1999, 1, 2045. 7. Fischer, C.; Carreira, E. M. Org. Lett. 2001, 3, 4319. 8. Wei, C.; Li, C.-J. J. Am. Chem. Soc. 2003, 125, 9584. 9. Matsuyama, N. et al. J. Org. Chem. 2009, 74, 3576. Safety
Packaging Under Nitrogen Alkynylsilane 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. Ethynyltrimethylsila
ne; Trimethylsilylacetyl
ene
Vapor pressure, 20 °C: 214 mm
Useful in Sonogashira reactions with differentiated reactivity at each terminus leading to unsymmetrical diaryl acetylenes
Reacts with aryl aldehydes to give diethynylmethanes (1,4-diynes)
Doped polymer films are conductive
Ethynylates aromatic compounds
Precursor to trimethylsilylethyny
l copper reagent
Lithiated derivative (n-BuLi treatment) reacts with halotriazines to produce monomers
Employed in ortho ethenylation of phenols
Undergoes Diels-Alder reactions with butadienes
Converts imines to propargyl amines
Forms propargylic amines from aldehydes and amines in aqueous system
Regioselectively forms either regioisomeric enyne upon addition to propargyl amines depending on catalyst employed
Reacts with aryl aldehydes to form diethynylmethane derivatives
Useful in the preparation of unsymmetrical diarylacetylenes
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
