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Synfacts 2010(2): 0211-0211  
DOI: 10.1055/s-0029-1219068
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart ˙ New York

Pt-Catalyzed Reduction of Carboxamides Using Hydrosilanes

Contributor(s):Paul Knochel, Tobias Thaler
S. Hanada, E. Tsutsumi, Y. Motoyama, H. Nagashima*
Kyushu University, Fukuoka, Japan
Practical Access to Amines by Platinum-Catalyzed Reduction of Carboxamides with Hydrosilanes: Synergy of Dual Si-H Groups Leads to High Efficiency and Selectivity
J. Am. Chem. Soc.  2009,  131:  15032-15040  
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Publication History

Publication Date:
21 January 2010 (online)

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Key words

platinum - reduction - hydrosilanes - carboxamides - amines

Significance

In this comprehensive article the platinum-catalyzed reduction of carbamides using hydrosilanes is described in detail. The reaction is highly chemoselective and proceeds with a ­remarkably high tolerance towards functional groups that are also prone to reduction, including cyano, ester and even nitro groups.

Comment

The key feature of this reaction is the ‘dual Si-H effect’ in which two proximate Si-H groups cooperatively promote the reduction reaction. Inexpensive and readily available disiloxanes, such as TMDS, can be used. The use of poly­methylhydrosiloxane (PHMS) has the advantage that the silicone and platinum species can easily be removed from the product.

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