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
Further Information

Publication History

Publication Date:
17 December 2012 (online)

 

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).


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).