Efficient and Practical Catalytic Oxidation of Alcohols Using Molecular Oxygen

Markó, István E.; Gautier, Arnaud; Chellé-Regnaut, Isabelle; Giles, Paul R.; Tsukazaki, Masao; Urch, Christopher J.; Brown, Stephen M.

doi:10.1021/jo980770h

Cited by 100 publications

(25 citation statements)

References 15 publications

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“…Serious drawbacks of the system are the low activity, the need for two equivalents of K 2 CO 3 (relative to substrate), and the expensive DBAD as a cocatalyst. According to a later report [111] the amount of K 2 CO 3 can be reduced to 0.25 equivalents by changing the solvent to fluorobenzene.…”

Section: ð5:13þmentioning

confidence: 99%

Modern Oxidation of Alcohols Using Environmentally Benign Oxidants

Arends

Sheldon

2010

Modern Oxidation Methods

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Section: ð5:13þmentioning

confidence: 99%

Modern Oxidation of Alcohols Using Environmentally Benign Oxidants

Arends

Sheldon

2010

Modern Oxidation Methods

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“…Among the various transition metal complexes reported [9][10][11][12][13][14][15][16][17], the amino acid Schiff base complexes have been proven to be excellent catalysts for catalytic epoxidation [13,14]. However, such homogeneous complexes suffer from the drawbacks of poor catalyst recovery and product separation [18].…”

Section: Introductionmentioning

confidence: 98%

Epoxidation of Styrene with H2O2 Catalyzed by Alanine–Salicylaldehyde Schiff Base Chromium (III) Complexes Immobilized on Mesoporous Materials

Wang

Wei

et al. 2010

Catal Lett

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Alanine-salicylaldehyde Schiff base chromium (III) complex was immobilized on mesoporous silica gel (SiO 2 ), MCM-41 and SBA-15. The resulting immobilized complexes were promising catalysts for the epoxidation of styrene with 30% hydrogen peroxide, and they all showed much higher catalytic performance than their homogeneous analogue. Simultaneously, the catalytic performance of immobilized complexes was found to be closely related to the textual and surface properties of the supports used. The complex immobilized on methyl-containing MCM-41 exhibited the highest catalytic performance. Under optimal reaction conditions, the highest conversion of styrene reached 80.2% with 77.0% selectivity to epoxide. In addition, the catalytic performance remained stable after six times of recycling.

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“…Markó et al have done pioneering work in this field and developed three generations of CuClphenanthroline catalytic systems, associated with di-tert-butyl hydrazine-1,2-dicarboxylate (DBADH 2 ) and strong base, for aerobic oxidation of alcohols [21][22][23][24][25]. Also, there has been significant interest in using the free radical TEMPO (2,2,6,6-tetramethyl-piperidinyl-1-oxy) or analogues as efficient co-catalysts in the aerobic oxidation of alcohols [26][27][28][29][30][31][32][33].…”

Section: Introductionmentioning

confidence: 99%

Room temperature aerobic oxidation of alcohols using CuBr2 with TEMPO and a tetradentate polymer based pyridyl-imine ligand

Kerton

2012

Applied Catalysis A: General

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Abstract.A series of tetradentate pyridyl-imine terminated Schiff-base ligands has been investigated for their ability in the catalytic oxidation of alcohols when combined with copper bromide (CuBr 2 ) and 2,2,6,6-tetramethylpiperidyl-1-oxy (TEMPO). Analogous bidentate ligands showed poorer catalytic activity and the ratio of Cu:ligand was of crucial importance in maintaining high yields. The polydimethylsiloxane (PDMS) derived pyridyl-imine terminated ligand combined with copper (II) ions affords an effective and selective catalyst for aerobic oxidations of primary and secondary alcohols under aqueous conditions. Preliminary mechanistic studies suggest that bimetallic complexes may be playing a role in the catalytic transformation. Graphical Abstract1

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Efficient and Practical Catalytic Oxidation of Alcohols Using Molecular Oxygen

Cited by 100 publications

References 15 publications

Modern Oxidation of Alcohols Using Environmentally Benign Oxidants

Modern Oxidation of Alcohols Using Environmentally Benign Oxidants

Epoxidation of Styrene with H2O2 Catalyzed by Alanine–Salicylaldehyde Schiff Base Chromium (III) Complexes Immobilized on Mesoporous Materials

Room temperature aerobic oxidation of alcohols using CuBr2 with TEMPO and a tetradentate polymer based pyridyl-imine ligand

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