Download PDF
Synfacts 2010(9): 1077-1077  
DOI: 10.1055/s-0030-1257987
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart ˙ New York

Immobilization of Organic Functional Groups onto Silica

Contributor(s):Yasuhiro Uozumi, Yoichi M. A. Yamada, Toshihiro Watanabe
J.-W. Park, C.-H. Jun*
Yonsei University, Seoul, South Korea
Transition-Metal-Catalyzed Immobilization of Organic Functional Groups onto Solid Supports through Vinylsilane Coupling Reactions
J. Am. Chem. Soc.  2010,  132:  7268-7269  
CrossrefGoogle Scholar
Further Information

Publication History

Publication Date:
23 August 2010 (online)

 PDF Download Permissions and Reprints

Key words

dimethyldivinyl-silane - transition-metal catalysis - surface modification - silica

Significance

Functionalized vinylsilanes 3 were prepared by hydroacylation of dimethyldivinylsilane (2) with various aldehydes 1 in the presence of (Ph3P)3RhCl, 2-amino-3-picoline, and 4-(trifluoromethyl)benzoic acid (63-92% yield, 11 examples). Immobilization of 3 onto silica by using [IrCl(coe)2]2 and DMA˙HCl gave the corresponding functionalized silica compounds 4 with 0.58-1.04 mmol/g of loading (11 examples).

Comment

The silica-immobilization method {[IrCl(coe)2]2; DMA˙HCl} has been developed by the same authors (Org. Lett. 2007, 9, 4073). Surface modification of hydrophilic glass slides with vinylsilanes 3e-g gave the significantly hydro­phobic glass slides 9e-g as estimated from contact angle measurements.

   Permissions and Reprints