Journal
APPLIED ORGANOMETALLIC CHEMISTRY
Volume 28, Issue 7, Pages 517-522Publisher
WILEY
DOI: 10.1002/aoc.3156
Keywords
hydrosilylation; rhodium; hydrogen; asymmetric catalysis; silanes
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Funding
- Conseil Regional de Bourgogne [PARI SMT 08 IME - Region Bourgogne]
- Ministere de l'Enseignement Superieur et de la Recherche
- Centre National de la Recherche Scientifique (CNRS)
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The influence of hydrogen pressure on the hydrosilylation of ketones catalyzed by [((S)-SYNPHOS)Rh(nbd)]OTf has been studied. We have notably demonstrated that hydrogen significantly affected the outcome of the reaction while not being consumed as stoichiometric reducing agent. In THF, diethyl ether or toluene, the hydrogen pressure exceedingly accelerated the hydrosilylation reaction and preserved or even improved the enantioselectivity of the process. In CH2Cl2, the rhodium catalyst also showed generally higher catalytic activity under hydrogen pressure. Most serendipitously, several ketones were found to give products of absolute opposite configuration upon performing the hydrosilylation under argon atmosphere or under hydrogen pressure. Copyright (c) 2014 John Wiley & Sons, Ltd.
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