Ethynyl-t-butyldimethylsilane

• CAT Number: M000788
• CAS Number: 86318-61-8
• Molecular Formula: C8H16Si
• Molecular Weight: 140.301
• Purity: ≥95%
• Synonyms: ETHYNYL-TERT-BUTYLDIMETHYLSILANE;(T-BUTYLDIMETHYLSILYL)ACETYLENE;TERT-BUTYLDIMETHYLSILYLACETYLENE;tert-BUTYLDIMETHYLSILYLACETYLENE 98%;ethynyl-t-butyldimethylsilane;(tert-Butyldimethylsilyl)ethyne;1-(tert-Butyldimethylsilyl)ethyne;3,3,4,4-Tetramethyl
• Storage: RT
• IUPAC Name: tert-butyl-ethynyl-dimethylsilane
• InChI: InChI=1S/C8H16Si/c1-7-9(5,6)8(2,3)4/h1H,2-6H3
• InChIKey: RTYNRTUKJVYEIE-UHFFFAOYSA-N
• SMILES: CC(C)(C)[Si](C)(C)C#C

Ethynyl-t-butyldimethylsilane (CAS 86318-61-8) is a bulky trialkylsilyl-protected alkyne. It participates in Cadiot-Chodkiewicz cross-coupling reaction with various bromoalkynes to afford synthetically useful unsymmetrical diynes. It readily undergoes cross-dimerization reaction with various internal phenyl acetylenes in the presence of rhodium dimers and bidentate phosphine ligands to afford enynes. Ethynyl-t-butyldimethylsilane may be used in the synthesis of β-alkynylketone and β-alkynyl aldehydes.

Reference

1. J Am Chem Soc. 2008 Feb 6;130(5):1576-7. doi: 10.1021/ja710540s. Epub 2008 Jan 16.Steric tuning of silylacetylenes and chiral phosphine ligands for rhodium-catalyzed asymmetric conjugate alkynylation of enones.Nishimura T(1), Guo XX, Uchiyama N, Katoh T, Hayashi T.


2.J Org Chem. 2002 Sep 20;67(19):6841-4. doi: 10.1021/jo025745x.Bulky trialkylsilyl acetylenes in the Cadiot-Chodkiewicz cross-coupling reaction.Marino JP(1), Nguyen HN.

 

Bulky trialkylsilyl-protected alkynes such as triethylsilyl (TES), tert-butyldimethylsilyl (TBS), and triisopropylsilyl (TIPS) acetylenes underwent the Cadiot-Chodkiewicz cross-coupling reaction with different bromoalkynes to form a variety of synthetically useful unsymmetrical diynes in good yields. The diyne alcohol 10 was transformed regio- and stereoselectively into enynes by hydrotelluration, carbometalation, and reduction reactions.

3.Angew Chem Int Ed Engl. 2009;48(43):8057-9. doi: 10.1002/anie.200904486.Asymmetric synthesis of beta-alkynyl aldehydes by rhodium-catalyzed conjugate alkynylation.Nishimura T(1), Sawano T, Hayashi T.

4.John Wiley & Sons, 2015.Modern alkyne chemistry: Catalytic and atom-economic transformations.Trost, Barry M., and Chao-Jun Li, eds.