Hydrogenation of Hindered Ketones with a Silica-Supported
Rh complex

S. Kawamorita; G. Hamasaka; H. Ohmiya; K. Hara; A. Fukuoka; M. Sawamura

doi:10.1055/s-0028-1087248

Subscribe to RSS

Please copy the URL and add it into your RSS Feed Reader.

https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000131.xml

Share / Bookmark

Facebook X Linkedin Weibo

Download PDF

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

Further Information

Publication History

Publication Date:
18 December 2008 (online)

Permissions and Reprints

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).