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Synfacts 2011(10): 1137-1137
DOI: 10.1055/s-0030-1261087
DOI: 10.1055/s-0030-1261087
Polymer-Supported Synthesis
© Georg Thieme Verlag
Stuttgart ˙ New York
Cycloaddition of Tetramethyldisiloxane to Alkynes with [Au]/TiO2
Contributor(s):Yasuhiro Uozumi, Go HamasakaI. N. Lykakis, A. Psyllaki, M. Stratakis*
University of Crete, Iraklion, Greece
Oxidative Cycloaddition of 1,1,3,3-Tetramethyldisiloxane to Alkynes Catalyzed by Supported Gold Nanoparticles
J. Am. Chem. Soc. 2011, 133: 10426-10429
University of Crete, Iraklion, Greece
Oxidative Cycloaddition of 1,1,3,3-Tetramethyldisiloxane to Alkynes Catalyzed by Supported Gold Nanoparticles
J. Am. Chem. Soc. 2011, 133: 10426-10429
Further Information
Publication History
Publication Date:
20 September 2011 (online)
Key words
cycloaddition - 1,1,3,3-tetramethyl-disiloxane - alkynes - gold nanoparticles - titanium(IV) oxide - heterogeneous catalysis
Significance
TiO2-supported gold nanoparticles ([Au]/TiO2) catalyzed the oxidative cycloaddition of 1,1,3,3-tetramethyldisiloxane (TMDS) to alkynes 1 to give the corresponding cycloadducts 2 in up to 99% isolated yield (22 examples, eq. 1).
Comment
The authors proposed a reaction pathway for the present oxidative cycloaddition as follows (eq. 2): (1) oxidative addition of TMDS to [Au] giving H-[Au]-Me2SiOSiHMe2 (A); (2) insertion of alkynes 1 into the Si-Au bond forming gold adducts B; (3) intramolecular elimination of H2 and [Au] to give cycloadducts 2.