Aqueous Phase C−H Bond Oxidation Reaction of Arylalkanes Catalyzed by a Water-Soluble Cationic Ru(III) Complex [(pymox-Me2)2RuCl2]+BF4

The cationic complex [(pymox-Me2)RuCl2]+BF4 − was found to be a highly effective catalyst for the C−H bond oxidation reaction of arylalkanes in water. For example, the treatment of ethylbenzene (1.0 mmol) with t-BuOOH (3.0 mmol) and 1.0 mol % of the Ru catalyst in water (3 mL) cleanly produced PhCOC...

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Published inOrganic letters Vol. 11; no. 7; pp. 1567 - 1569
Main Authors Yi, Chae S, Kwon, Ki-Hyeok, Lee, Do W
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 02.04.2009
Amer Chemical Soc
Subjects
Alkanes - chemistry
Catalysis
Chemistry
Chemistry, Organic
Combinatorial Chemistry Techniques
Kinetics
Molecular Structure
Organometallic Compounds - chemistry
Oxidation-Reduction
Physical Sciences
Ruthenium - chemistry
Science & Technology
Water - chemistry
ALCOHOLS
ACTIVATION
EFFICIENT OXYGENATION
ACID
HYDROCARBONS
ORGANIC-REACTIONS
CHEMISTRY
RUTHENIUM
INTERMEDIATE
ALKANES
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Summary:The cationic complex [(pymox-Me2)RuCl2]+BF4 − was found to be a highly effective catalyst for the C−H bond oxidation reaction of arylalkanes in water. For example, the treatment of ethylbenzene (1.0 mmol) with t-BuOOH (3.0 mmol) and 1.0 mol % of the Ru catalyst in water (3 mL) cleanly produced PhCOCH3 at room temperature. Both a large kinetic isotope effect (k H/k D = 14) and a relatively large Hammett value (ρ = −1.1) suggest a solvent-caged oxygen rebounding mechanism via a Ru(IV)-oxo intermediate species.
Bibliography:NIH RePORTER
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ISSN:1523-7060
1523-7052
DOI:10.1021/ol900097y