Aqueous “Green” Organometallic Chemistry: Structure of the Molybdocene Monohydride Used for Carbonyl Reduction in Water
journal contributionposted on 18.10.2001, 00:00 by Louis Y. Kuo, Timothy J. R. Weakley, Kukui Awana, Clara Hsia
The compound bis(η5-cyclopentadienyl)hydridomolybdenum(IV) triflate, which was synthesized from Cp2MoH2 and methyl triflate, is water soluble and undergoes hydride deuteride exchange in D2O. The molybdocene monohydride reduces ketones and aldehydes in water under mild aqueous conditions (pH 7 and 40 °C), which underscores the utility of this metallocene hydride for further organic transformations. Mechanistic features for the ketone → alcohol reduction suggest that either the reduction process is promoted by acid protonation of the carbonyl oxygen or it follows the reverse pathway of the aqueous C−H activation of primary alcohols by Cp2MoCl2(aq) reported earlier by Balzarek and Tyler.
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Carbonyl ReductioncyclopentadienylD 2 OOrganometalliccarbonyl oxygenhydride deuteride exchangeMechanistic featuresutilitypH 7Molybdocene Monohydridealdehydetransformationactivationbimetallocene hydridecompoundaqmethyl triflateacid protonationreduction processAqueouCp 2 MoH 2Tylermolybdocene monohydrideketoneCp 2 MoCl 2Balzarekpathway