Hydrogenation of Hindered Ketones with a Silica-Supported
Rh complex

doi:10.1055/s-0028-1087248

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Synfacts 2009(1): 0107-0107
DOI: 10.1055/s-0028-1087248

Polymer-Supported Synthesis

Hydrogenation of Hindered Ketones with a Silica-Supported Rh complex

Contributor(s): Yasuhiro Uozumi, Takao Osako
S. Kawamorita, G. Hamasaka, H. Ohmiya, K. Hara, A. Fukuoka, M. Sawamura*
Hokkaido University, Sapporo, Japan

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Publikationsdatum:
18. Dezember 2008 (online)

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Significance

A silica-supported compact phosphine-Rh complex [silica-SMAP-Rh(OMe)(cod)] catalyzed the hydrogenation of hindered ketones in the presence of Et₃N under 5 atm of hydrogen pressure to afford the corresponding alcohols in 70-100% yield (13 examples). Although the hydrogenation of di-tert-butyl ketone with silica-SMAP-Rh(OMe)(cod) did not proceed under 5 atm of H₂ at 23 ˚C, the complete conversion to di-tert-butylmethanol was accomplished under more forcing conditions (30 atm of H₂, 100 ˚C, 48 h).