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Hydrosilanes Are Not Always Reducing Agents for Carbonyl Compounds but Can Also Induce Dehydration: A Ruthenium‐Catalyzed Conversion of Primary Amides to Nitriles
Author(s) -
Hanada Shiori,
Motoyama Yukihiro,
Nagashima Hideo
Publication year - 2008
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200800523
Subject(s) - chemistry , dehydration , ruthenium , catalysis , reducing agent , dehydration reaction , primary (astronomy) , organic chemistry , combinatorial chemistry , biochemistry , physics , astronomy
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)