Hydrosilanes Are Not Always Reducing Agents for Carbonyl Compounds but Can Also Induce Dehydration: A Ruthenium-Catalyzed Conversion of Primary Amides to Nitriles

✍ Scribed by Shiori Hanada; Yukihiro Motoyama; Hideo Nagashima

• Publisher: John Wiley and Sons
• Year: 2008
• Tongue: English
• Weight: 124 KB
• Volume: 2008
• Category: Article
• ISSN: 1434-193X
• DOI: 10.1002/ejoc.200800523

✦ Synopsis

Abstract

A practical procedure for production of nitriles is offered by the triruthenium carbonyl cluster catalyzed dehydration of primary carboxamides with hydrosilanes under neutral conditions. This is the first example that a transition‐metal‐catalyzed activation of Si–H bonds does not lead to the reduction of carbonyl compounds but to dehydration. Possible mechanisms for the dehydration is discussed on the basis of NMR spectroscopic detection of intermediary species. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)