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Synfacts 2009(3): 0339-0339  
DOI: 10.1055/s-0028-1087733
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart ˙ New York

[Silica]-SMAP-Rh System for the Hydrosilylation of Hindered Ketones

Contributor(s): Yasuhiro Uozumi, Yoichi M. A. Yamada, Hidetoshi Ohta
G. Hamasaka, S. Kawamorita, A. Ochida, R. Akiyama, K. Hara, A. Fukuoka, K. Sakura, W. J. Chun, H. Ohmiya, M. Sawamura*
Hokkaido University, Sapporo and International Christian University, Tokyo, Japan
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Publication History

Publication Date:
19 February 2009 (online)

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Significance

Silica gel-supported SMAPs, [silica gel 60N]-SMAP (4A) and [CARiACT Q-10]-SMAP (4B), consisting of a compact trialkylphosphine (SMAP) were prepared. Thus, the reaction of Ph-SMAP (1) with TfOH afforded silyl triflate 2. Surface treatment of silica gel 60N and CARiACT Q-10 with 2 gave phosphine-functionalized silica gels 3A and 3B. The surface silanols were end-capped with Me3Si group to afford 4A and 4B. Hydrosilylation of ketones 5a-i with triorganosilanes 6a-c was carried out in the presence of [RhCl(C2H4)2]2 and 4A or 4B to give the silyl ethers 7 (27 examples, 91-100% yield).