| 1.Research Institution | @ | Osaka University |
| @ | ||
| 2.Research Area | @ | Physical and Engineering Sciences |
| @ | ||
| 3.Research Field | @ | Advanced Processes |
| @ | ||
| 4.Term of Project | @ | FY1996`FY2000 |
| @ | ||
| 5.Project Number | @ | 96P00301 |
| @ | ||
| 6.Title of Project | @ | Environmentally Friendly Catalytic Process |
| Name | Institution,Department | Title of Position |
| Shun-Ichi Murahashi | Osaka University, Graduate School of Engineering Science | Prof. |
8.Core Members
| Names | Institution,Department | Title of Position |
| Yasutaka Ishii | Kansai University, Faculty of Engineering | Prof. |
| Kiyotomi Kaneda | Osaka University, Graduate School of Engineering Science | Prof. |
9.Cooperating Researchers
| Names | Institution,Department | Title of Position |
| Takeshi Naota | Osaka University, Graduate School of Engineering Science | Assoc. Prof. |
| Yasushi Imada | Osaka University, Graduate School of Engineering Science | Assoc. Prof. |
| Yutaka Nishiyama | Kansai University, Faculty of Engineering | Assoc. Prof. |
10.Summary of Research Results
|
The main aim of the present research project is to acquire innovative method for organic transformations that satisfies future social requirement for atom economy and sustainability. 1) Catalytic Oxidations Simulated by Enzymatic Functions: Based on the new strategy for simulating enzymatic function of cytochrome P-450 monooxygenases with transition metal catalysis, the generation, reactivity and catalysis of various oxometal species of transition metals have been investigated from synthetic viewpopoints. A variety of specific oxygenation reactions of amines, phenols and alkanes can be performed with homogeneous and heterogeneous metal catalysts with oxidants such as peroxides and molecular oxygen. 2) Development of Aerobic Oxidations Mediated by Radical Species: A new methodology for the catalytic aerobic oxidations has been developed using N-hydroxyphthalimide (NHPI) as a radical mediator. Various oxidative transformations of alkanes such as oxidative cleavage, nitration and sulfoxidation can be performed under oxygen atmosphere with a catalytic amount of metal complexes and NHPI. 3) Development of Organic Transformations with Redox Lewis Acid and Base Catalysts: Low valent metal complexes bearing low redox potentials have proven to act as efficient Lewis acid and base catalysts for various organic transformations, which include hydration, amidation, and esterification of nitriles, aldol condensations, Michael additions, and so on. |
11.Key Words
(1)Oxidation of AlkanesA(2)Oxidation of AminesA(3)Oxidation of Alkenes
(4)Aerobic OxidationsA(5)Ruthenium CatalystsA(6)Hydrotalcites
(7)NitrilesA(8)C-H ActivationA(9)N-Hydroxyphthalimide
12.References
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| Journal | Volume | Year | Pages Concerned | |
| Tetrahedron Lett. | 37 | 1996 | 1633-1636 | |
| Author | Title of Article | |||
| S. -I. Murahashi | Ruthenium-Catalyzed Oxidation of Phenols with Alkyl Hydroperoxides. A Novel, Facile Route to 2-Substituted Quinones | |||
| Journal | Volume | Year | Pages Concerned | |
| J. Am. Chem. Soc. | 118 | 1996 | 2509-2510 | |
| Author | Title of Article | |||
| S. -I. Murahashi | Ruthenium-Catalyzed Oxidations of Alcohols | |||
| Journal | Volume | Year | Pages Concerned | |
| Russian J. Org. Chem. (Zhurnal Organicheskoi Khimii). | T32 | 1996 | 223-232 | |
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| T. Hosokawa | A Chiral Amidophosphine Bearing a P-N Bond and Its p-Allyl Palladium(II)Chemistry | |||
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| Journal | Volume | Year | Pages Concerned | |
| Bull. Chem. Soc. Jpn. | 69 | 1996 | 2079-2090 | |
| Author | Title of Article | |||
| S. -I. Murahashi | A New Way for Efficient Catalysis by Using Low Valent Ruthenium Complexes as Redox Lewis Acid and Base Catalysts | |||
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| Journal | Volume | Year | Pages Concerned | |
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| Author | Title of Article | |||
| S. -I. Murahashi | Synthesis of (R)-and (S)-3-(tert-Butyldimethylsilyloxy)-l-Pyrroline N-Oxides-Chiral Nitrones for Synthesis of Biologically Active Pyrrolidine Derivative, Geissman-Waiss Lactone | |||
| Journal | Volume | Year | Pages Concerned | |
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| Author | Title of Article | |||
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| Journal | Volume | Year | Pages Concerned | |
| Catal. Today | 41 | 1998 | 339-349 | |
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| T. Kawakami | Asymmetric Synthesis of ƒÀ-Amino Acids by Addition of Chiral Enolates to N-Acyloxy-iminium Ions and Application for Synthesis of Optically Active 5-Substituted 8-Methylindolizidines | |||
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| Journal | Volume | Year | Pages Concerned | |
| Bull. Chem. Soc. Jpn. | 72 | 1999 | 2737-2754 | |
| Author | Title of Article | |||
| S. -I. Murahashi | Synthesis of Homochiral ƒÀ-Sulfinyl Nitrones and Their Application for Enantioselective Synthesis of(+)-Euphococcinine | |||
| Journal | Volume | Year | Pages Concerned | |
| Heterocycles | 52 | 2000 | 557-561 | |
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| Journal | Volume | Year | Pages Concerned | |
| Peptide Science 1999 | @ | 2000 | 137-140 | |
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| S. -I. Murahashi | Synthesis of Optically Active N-Hydroxylamines by Asymmetric Hydrogenation of Nitrones with Iridium Catalysts | |||
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| Chem. Commun. | @ | 2000 | 409-410 | |
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| Journal | Volume | Year | Pages Concerned | |
| Acc. Chem. Res. | 33 | 2000 | 225-233 | |
| Author | Title of Article | |||
| S. -I. Murahashi | Aldol and Michael Reactions of Nitriles Catalyzed by Cyclopentadienylruthenium Enolate Complexes | |||
| Journal | Volume | Year | Pages Concerned | |
| Synlett | 7 | 2000 | 1016-1018 | |
| Author | Title of Article | |||
| S. -I. Murahashi | Exploitation of Environmentally Friendly Catalytic Processes | |||
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| Gratama Workshop 2000, Conference Report | @ | 2000 | 37-39 | |
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| Bull. Chem. Soc. Jpn. | 72 | 2000 | 2423-2444 | |
| Author | Title of Article | |||
| S. -I. Murahashi | Ruthenium-Catalyzed Oxidation of Alkenes with tert-Butyl Hydroperoxide and Peracetic Acid | |||
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| Author | Title of Article | |||
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| Journal | Volume | Year | Pages Concerned | |
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| Journal | Volume | Year | Pages Concerned | |
| Synlett | @ | 2001 | in press | |
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| Author | Title of Article | |||
| S. Ueno | The Active Sites in the Heterogeneous Baeyer-Villiger Oxidation of Cyclopentanone by Hydrotalcite Catalysts | |||
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| Author | Title of Article | |||
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| S. Ueno | Hydrotalcite Catalysis: Heterogeneous Epoxidation of Olefins Using Hydrogen Peroxide in the Presence of Nitrile | |||
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| Chem. Commun. | @ | 1998 | 295-296 | |
| Author | Title of Article | |||
| K. Kaneda | Heterogeneous Oxidation of Allylic and Benzylic Alcohols Catalyzed by Ru-Mg-Al Hydrotalcites in the Presence of Molecular Oxygen | |||
| Journal | Volume | Year | Pages Concerned | |
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| Author | Title of Article | |||
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| Author | Title of Article | |||
| T. Matsushita | Highly Efficient Oxidation of Alcohols and Aromatic Compounds Catalysed by Ru-Co-Al Hydrotalcite in the Presence of Molecular Oxygen | |||
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| Author | Title of Article | |||
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| Journal | Volume | Year | Pages Concerned | |
| Langmuir | 15 | 1999 | 3557-3562 | |
| Author | Title of Article | |||
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| Journal | Volume | Year | Pages Concerned | |
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| J. Mol. Cat. A: Chemical | 145 | 1999 | 329-333 | |
| Author | Title of Article | |||
| K. Kaneda | Catalyst Design of Polymer-Bound Metal Complexes in Selective Reduction of Organic Compounds | |||
| Journal | Volume | Year | Pages Concerned | |
| Trends in Organometallic Chemistry | 3 | 1999 | 179-200 | |
| Author | Title of Article | |||
| K. Ebitani | Preparation of Zeolite X-Encapsulated Copper(II) Chloride Complex and Its Catalysis for Liquid-Phase Oxygenation of Enamines in the Presence of Molecular Oxygen | |||
| Journal | Volume | Year | Pages Concerned | |
| Chem. Commun. | @ | 2000 | 869-870 | |
| Author | Title of Article | |||
| K. Ebitani | Simple and Clean Synthesis of 9, 9-Bis[4-(2-hydroxyethoxy)phenyl]fluorene from Aromatic Alkylation of Phenoxyethanol with Fluoren-9-one Catalysed by Titanium Cation-Exchanged Montmorillonite | |||
| Journal | Volume | Year | Pages Concerned | |
| Green Chemistry | 2 | 2000 | 157-160 | |
| Author | Title of Article | |||
| K. Yamaguchi | Creation of a Monomeric Ru Species on the Surface of Hydroxyapatite as an Efficient Heterogeneous Catalyst for Aerobic Alcohol Oxidation | |||
| Journal | Volume | Year | Pages Concerned | |
| J. Am. Chem. Soc. | 122 | 2000 | 7144-7145 | |
| Author | Title of Article | |||
| K. Kaneda | Catalyst Design of Hydrotalcite Compounds for Efficient Oxidations | |||
| Journal | Volume | Year | Pages Concerned | |
| Catalysis Surveys from Japan | 4 | 2000 | 31-38 | |
| Author | Title of Article | |||
| K. Yamaguchi | Epoxidation of ƒ¿, ƒÀ-Unsaturated Ketones Using Hydrogen Peroxide in the Presence of Basic Hydrotalcite Catalysts | |||
| Journal | Volume | Year | Pages Concerned | |
| J. Org. Chem. | 65 | 2000 | 6897-6903 | |
| Author | Title of Article | |||
| K. Yamaguchi | Creation of a Monomeric Ru Species on the Surface of Hydroxyapatite as an Efficient Heterogeneous Catalyst for Aerobic Alcohol Oxidation | |||
| Journal | Volume | Year | Pages Concerned | |
| J. Am. Chem. Soc. | 122 | 2000 | 7144-7145 | |
| Author | Title of Article | |||
| K. Kaneda | Catalyst Design of Hydrotalcite Compounds for Efficient Oxidations | |||
| Journal | Volume | Year | Pages Concerned | |
| Catalysis Surveys from Japan | 4 | 2000 | 31-38 | |
| Author | Title of Article | |||
| K. Yamaguchi | Epoxidation of ƒ¿, ƒÀ-Unsaturated Ketones Using Hydrogen Peroxide in the Presence of Basic Hydrotalcite Catalysts | |||
| Journal | Volume | Year | Pages Concerned | |
| J. Org. Chem. | 65 | 2000 | 6897-6903 | |
| Author | Title of Article | |||
| K. Nagashima | Preparation of Highly Dispersed Cu on TiO2 Using Cu(II) | |||
| Journal | Volume | Year | Pages Concerned | |
| Chem. Lett. | @ | 2000 | 264-265 | |
| Author | Title of Article | |||
| H. Zhu | Synthesis of Dimethylaminoethyl Chitin and Applicatrions as a Polymeric Ligand to Form Rh Cluster Complexes for the Reduction of Benzaldehyde and Nitrobenzene | |||
| Journal | Volume | Year | Pages Concerned | |
| Macromol. Chem. Phys. | 201 | 2000 | 1431-1435 | |
| Author | Title of Article | |||
| K. Ebitani | XAFS Study on Active Pr Sites in Zeolite as a Photocatalyst for Decomposition of Nitrous Oxide | |||
| Journal | Volume | Year | Pages Concerned | |
| Journal of Synchrotron Radiation | 8 | 2001 | 481-483 | |
| Author | Title of Article | |||
| K. Mori | Catalysis of a Hydroxyapatite-Bound Ru Complex: Efficient Heterogeneous Oxidation of Primary Amines to Nitriles in the Presence of Molecular Oxygen | |||
| Journal | Volume | Year | Pages Concerned | |
| Chem. Commun. | @ | 2001 | 461-462 | |
| Author | Title of Article | |||
| K. Kaneda | Design of High Performance Hydrotalcite Catalysts in Efficient Monooxygenation Type Reactions Using Hydrogen Peroxide | |||
| Journal | Volume | Year | Pages Concerned | |
| Recent Research Developments in Organic Chemistry | @ | 2001 | in press | |
| Author | Title of Article | |||
| T. Yokota | Cyclotrimerization of Alkynes Using a Multicatalytic System, Pd(II)/Chlorohydroquinone/NPMoV, under Dioxygen | |||
| Journal | Volume | Year | Pages Concerned | |
| Tetrahedron Lett. | 38 | 1997 | 3923-3926 | |
| Author | Title of Article | |||
| A. Hanyu | Selective Aerobic Oxidation of Isophorone Catalyzed by Molybdovanadophosphate Supported on Carbon (NPMoV/C) | |||
| Journal | Volume | Year | Pages Concerned | |
| Tetrahedron Lett. | 38 | 1997 | 5659 - 5662 | |
| Author | Title of Article | |||
| Y. Yoshino | Catalytic Oxidation of Alkylbenzenes with Molecular Oxygen under Normal Pressure and Temperature by N-Hydroxyphthalimide Combined with Co(OAc)2 | |||
| Journal | Volume | Year | Pages Concerned | |
| J. Org. Chem. | 62 | 1997 | 6810 - 6813 | |
| Author | Title of Article | |||
| H. Yamamoto | Selective Oxidation of Vinyl Ethers and Silyl Enol Ethers with Hydrogen Peroxide Catalyzed by Peroxotungstophosphate | |||
| Journal | Volume | Year | Pages Concerned | |
| J. Org. Chem. | 62 | 1997 | 7174 - 7177 | |
| Author | Title of Article | |||
| S. Sakaguchi | N-Hydroxyphthalimide(NHPI)-Catalyzed Reaction of Adamantane under Nitric Oxide Atmosphere | |||
| Journal | Volume | Year | Pages Concerned | |
| Tetrahedron Lett. | 38 | 1997 | 7075 - 7078 | |
| Author | Title of Article | |||
| S. Sakaguchi | An Efficient Aerobic Oxidation of Isobutane to t-Butyl Alcohol by N-Hydroxyphthalimide Combined with Co(II) Species | |||
| Journal | Volume | Year | Pages Concerned | |
| Bull. Chem. Soc. Jpn. | 71 | 1998 | 1237 - 1240 | |
| Author | Title of Article | |||
| T. Iwahama | Direct Conversion of Cyclohexane into Adipic Acid with Molecular Oxygen Catalyzed by N-Hydroxyphthalimide Combined with Mn(acac)2 and Co(OAc)2 | |||
| Journal | Volume | Year | Pages Concerned | |
| Org. Pro. Res. Dev. | 2 | 1998 | 255 - 260 | |
| Author | Title of Article | |||
| A. Hanyu | Selective Aerobic Oxidation of Primary Alcohols Catalyzed by a Ru(PPh3)3Cl2/Hydroquinone System | |||
| Journal | Volume | Year | Pages Concerned | |
| Tetrahedron Lett. | 39 | 1998 | 5557 - 5560 | |
| Author | Title of Article | |||
| S. Sakaguchi | Oxygenation of Alkynes to ƒ¿, ƒÀ-Acetylenic Ketones with Dioxygen Catalyzed by N-Hydroxyphthalimide Combined with a Transition Metal | |||
| Journal | Volume | Year | Pages Concerned | |
| Chem. Commun. | @ | 1998 | 2037 - 2038 | |
| Author | Title of Article | |||
| T. Iwahama | Selective Oxidation of Sulfides to Sulfoxides with Molecular Oxygen Catalyzed by N-Hydroxyphthalimide (NHPI) in the Presence of Alcohols | |||
| Journal | Volume | Year | Pages Concerned | |
| Tetrahedron Lett. | 39 | 1998 | 9059 - 9062 | |
| Author | Title of Article | |||
| Y. Sakurai | Carbonylation of Terminal Alkynes Using a Multicatalytic System, Pd(II)/Chlorohydroquinone/NPMoV, under Carbon Monoxide and Dioxygen | |||
| Journal | Volume | Year | Pages Concerned | |
| Tetrahedron Lett. | 40 | 1999 | 1701 - 1704 | |
| Author | Title of Article | |||
| K. Matsunaka | A Remarkable Effect of Quaternary Ammonium Bromide for the N-Hydroxyhthalimide-Catalyzed Aerobic Oxidation of Hydrocarbons | |||
| Journal | Volume | Year | Pages Concerned | |
| Tetrahedron Lett. | 40 | 1999 | 2165 - 2168 | |
| Author | Title of Article | |||
| Y. Ishii | A New Strategy for Alkane Oxidation with O2 Using N-Hydroxyphthalimide (NHPI) as a Radical Catalyst | |||
| Journal | Volume | Year | Pages Concerned | |
| Catalysis Surveys from Japan | 3 | 1999 | 27 - 35 | |
| Author | Title of Article | |||
| T. Iwahama | Epoxidation of Alkenes Using Dioxygen in the Presence of an Alcohol Catalyzed by N-Hydroxyphthalimide and Hexafluoroacetone | |||
| Journal | Volume | Year | Pages Concerned | |
| Chem. Commun. | @ | 1999 | 727 - 728 | |
| Author | Title of Article | |||
| M. Eikawa | A New Approach for Oxygenation Using Nitric Oxide under the Influence of N-Hydroxyphthalimide | |||
| Journal | Volume | Year | Pages Concerned | |
| J. Org. Chem. | 64 | 1999 | 4676 - 4679 | |
| Author | Title of Article | |||
| S. Sakaguchi | Dehomologation of Aldehydes via Oxidative Cleavage of Silyl Enol Ethers with Aqueous Hydrogen Peroxide Catalyzed by Cetylpyridinium Peroxotungstphosphate under Two-Phase Conditions | |||
| Journal | Volume | Year | Pages Concerned | |
| J. Org. Chem. | 64 | 1999 | 5954 - 5957 | |
| Author | Title of Article | |||
| E. Takezawa | Oxidative Cleavage of vic-Diols to Aldehydes with Dioxygen Catalyzed by Ru(PPh3)3Cl2 on Active Carbon | |||
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| Org. Lett. | 1 | 1999 | 713 - 715 | |
| Author | Title of Article | |||
| T. Iwahama | Epoxidation of Alkenes using Alkyl Hydroperoxides Generated in situ by Catalytic Autoxidation of Hydrocarbons with Dioxygen | |||
| Journal | Volume | Year | Pages Concerned | |
| Chem. Commun. | @ | 2000 | 163 - 164 | |
| Author | Title of Article | |||
| T. Iwahama | Epoxidation of Alkenes with H2O2 Generated in situ from Alcohols and Molecular Oxygen using N-Hydroxyphthalimide and Hexafluoroacetone as Catalyst | |||
| Journal | Volume | Year | Pages Concerned | |
| Heterocycles | 52 | 2000 | 693 - 705 | |
| Author | Title of Article | |||
| T. Iwahama | Production of Hydrogen Peroxide via Aerobic Oxidation of Alcohols Catalyzed by N-Hydroxyphthalimide | |||
| Journal | Volume | Year | Pages Concerned | |
| Org. Pro. Res. Dev. | 4 | 2000 | 94 - 97 | |
| Author | Title of Article | |||
| T. Iwahama | Catalytic ƒ¿-Hydroxy Carbon Radical Generation and Addition. Synthesis of ƒ¿-Hydroxy-ƒÁ-Lactones from Alcohols, ƒ¿, ƒÀ-Unsaturated Esters and Dioxygen | |||
| Journal | Volume | Year | Pages Concerned | |
| Chem. Commun. | @ | 2000 | 613 - 614 | |
| Author | Title of Article | |||
| Y. Ishii | The First Catalytic Sulfoxidation of Saturated Hydrocarbons with SO2/O2 by a Vanadium Species | |||
| Journal | Volume | Year | Pages Concerned | |
| J. Am. Chem. Soc. | 122 | 2000 | 7390 - 7391 | |
| Author | Title of Article | |||
| T. Iwahama | Efficient Oxidation of Alcohols to Carbonyl Compounds with Molecular Oxygen Catalyzed by N-Hydroxyphthalimide Combined with a Co Species | |||
| Journal | Volume | Year | Pages Concerned | |
| J. Org. Chem. | 65 | 2000 | 6502-6507 | |
| Author | Title of Article | |||
| A. Shibamoto | Aerobic Oxidation of Methylpyridines to Pyridinecarboxylic Acids Catalyzed by N-Hydroxyphthalimide | |||
| Journal | Volume | Year | Pages Concerned | |
| Org. Pro. Res. Dev. | 4 | 2000 | 505-508 | |
| Author | Title of Article | |||
| T. Iwahama | Catalytic Radical Addition of Ketones to Alkenes by a Metal-Dioxygen Redox System | |||
| Journal | Volume | Year | Pages Concerned | |
| Chem. Commun. | @ | 2000 | 2317-2318 | |
| Author | Title of Article | |||
| T. Hirano | N-Hydroxyphthalimide-Catalyzed Radical Addition of 1, 3-Dioxolanes and Molecular Oxygen to Alkenes under Ambient Conditions: A New Route to ƒÀ -Oxycarbonyl Compounds | |||
| Journal | Volume | Year | Pages Concerned | |
| Chem. Commun. | @ | 2000 | 2457-2458 | |
| Author | Title of Article | |||
| S. Sakaguchi | An Efficient Catalytic Alkane Nitration with NO2 under Air Assisted by N-Hydroxyphthalimide | |||
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| Angew. Chem. Int. Ed. | 40 | 2001 | 222-224 | |
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| Y. Tashiro | A New Strategy for the Preparation of Terephthalic Acid by the Aerobic Oxidation of p-Xylene using N-Hydroxyphthalimide as a Catalyst | |||
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| Adv. Synth. Catal | 343 | 2001 | 220-225 | |
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| Kodansha, Tokyo | 1998 | 1-16 | |
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| S. -I. Murahashi | Novel Redox Lewis Acid and Base Catalysis for Activation of Nitriles and Carbonyl Compounds, in Reactive Organometallics | ||
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| Kodansha, Tokyo | 1998 | 17-20 | |
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| S. -I. Murahashi | Amine Oxidation, in Transition Metals for Organic Synthesis | ||
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| VCH, Weinheim | 1998 | 373-383 | |
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| S. -I. Murahashi | Bioinspired OxidationsCatalyzed by Ruthenium Complexes, in Biomimetic Oxidations by Transition Metal Catalyzed Reactions | ||
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| Imperial College Press, London | 1999 | 563-611 | |
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| T. Hosokawa | Palladium-catalyzed Oxidation of Alkenes, in Chemistry for the 21st Century Monographs: Transition Metal Catalyzed Reactions | ||
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| Blackwell Science, Oxford | 1999 | 329-341 | |
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| S. -I. Murahashi | Pd-Catalyzed Substitution Reactions of Nitrogen and Other Group 15 Atom Containing Allylic Derivatives, in Handbook of Organopalladium Chemistry for Organic Synthesis | ||
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| John Wiley &Sons, New York | 2001 | in press | |
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| S. -I. Murahashi | Intermolecular Oxypalladation Not Accompanied by Dehydrogenation, in Handbook of Organopalladium Chemistry for Organic Synthesis | ||
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| John Wiley &Sons, New York | 2001 | in press | |
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| S. -I. Murahashi | Oxidation of Amines, Alcohols, and Related Compounds, in Handbook of Organopalladium Chemistry for Organic Synthesis | ||
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| John Wiley &Sons, New York | 2001 | in press | |
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| K. Kaneda | Phosphinated Polystyrene-Bound Metal Complexes (Pd and Rh), in Polymeric Materials Encyclopedia | ||
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| CRC Press, New York | 1996 | 5067-5073 | |