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Synfacts 2013; 9(1): 0112
DOI: 10.1055/s-0032-1317908
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart · New York

Silylation of Alcohol Derivatives with 1,2-Disilanes Catalyzed by Au/TiO2

Contributor(s):
Yasuhiro Uozumi
,
Takao Osako
Gryparis C, Stratakis M * University of Crete, Iraklion, Greece
Gold Nanoparticles-Catalyzed Activation of 1,2-Disilanes: Hydrolysis, Silyl Protection of Alcohols and Reduction of tert-Benzylic Alcohols.

Chem. Commun. 2012;
48: 10751-10753
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Publication History

Publication Date:
17 December 2012 (online)

 
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Key words

gold nanoparticles - titanium dioxide - 1,2-disilanes - alcohols

Significance

Gold nanoparticles supported on titanium dioxide (Au/TiO2) catalyzed the silylation of water and primary, secondary, and tertiary aliphatic alcohols with 1,2-disilanes via Si–Si bond cleavage to give the corresponding silyl ethers in up to >99% yield (eq. 1). When tertiary benzylic alcohols were used for the reaction, the reduction proceeded to afford the corresponding alkanes as the major products (eq. 2).


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Comment

The authors previously reported the oxidative cycloaddition of 1,1,3,3-tetramethyldi­siloxane to alkynes catalyzed by Au/TiO2 (J. Am. Chem. Soc. 2011, 133, 10426). The catalytic activity of Au/TiO2 for the silylation of water was superior to that of gold nanoparticles supported on other supports such as aluminum oxide (Al2O3) and zinc oxide (ZnO).


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