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 in | Organic letters Vol. 11; no. 7; pp. 1567 - 1569 |
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| Main Authors | , , |
| Format | Journal Article |
| Language | English |
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02.04.2009
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| Abstract | 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. |
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| AbstractList | The cationic complex [(pymox-Me(2))RuCl(2)](+)BF(4)(-) 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 PhCOCH(3) at room temperature. Both a large kinetic isotope effect (k(H)/k(D) = 14) and a relatively large Hammett value (rho = -1.1) suggest a solvent-caged oxygen rebounding mechanism via a Ru(IV)-oxo intermediate species. 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. The cationic complex [(pymox-Me 2 )RuCl 2 ] + BF 4 - 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 PhCOCH 3 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. The cationic complex [(pymox-Me-2)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 (p -1.11) suggest a solvent-caged oxygen rebounding mechanism via a Ru(IV)-oxo intermediate species. |
| Author | Yi, Chae S Kwon, Ki-Hyeok Lee, Do W |
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| Snippet | 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... The cationic complex [(pymox-Me-2)RuCl2]+BF4- was found to be a highly effective catalyst for the C-H bond oxidation reaction of arylalkanes in water. For... The cationic complex [(pymox-Me(2))RuCl(2)](+)BF(4)(-) was found to be a highly effective catalyst for the C-H bond oxidation reaction of arylalkanes in water.... The cationic complex [(pymox-Me 2 )RuCl 2 ] + BF 4 - was found to be a highly effective catalyst for the C-H bond oxidation reaction of arylalkanes in water.... |
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| SubjectTerms | 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 |
| Title | Aqueous Phase C−H Bond Oxidation Reaction of Arylalkanes Catalyzed by a Water-Soluble Cationic Ru(III) Complex [(pymox-Me2)2RuCl2]+BF4 |
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