Aerobic oxidation of α-hydroxycarbonyls catalysed by trichlorooxyvanadium: efficient synthesis of α-dicarbonyl compounds

Kirihara, Masayuki; Ochiai, Yuta; Takizawa, Shinobu; Takahata, Hiroki; Nemoto, Hideo

doi:10.1039/a903622i

Cited by 129 publications

(45 citation statements)

References 8 publications

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“…From the standpoint of green and sustainable chemistry, in addition to safety considerations, it is of particular importance to develop an alternative approach to construct a cleaner and more efficient catalytic system for the selective oxidation of alcohols. In this context, much attention has been recently paid to the development of transition-metal-catalyzed aerobic alcohol oxidations that involve Ru, Pd, Au, Co, Cu, Pt, Rh, V, Os, Ce, and Ni [4] by using "green" molecular oxygen (even air) as oxidant. [2,5] Enhanced catalytic performances in both activity and selectivity, high atom economy, and cheaper and less polluting oxidants are involved in the latter processes.…”

Section: Introductionmentioning

confidence: 99%

A Tris(triazolate) Ligand for a Highly Active and Magnetically Recoverable Palladium Catalyst of Selective Alcohol Oxidation Using Air at Atmospheric Pressure

Wang

Deraedt

Salmon

et al. 2015

Chemistry A European J

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High efficiency and selectivity, easy magnetic recovery and recycling, and use of air as the oxidant at atmospheric pressure are major objectives for oxidation catalysis in terms of sustainable and green processes. A tris(triazolyl) ligand, so far only used in copper-catalyzed alkyne azide cycloadditions, was found to be extremely efficient in SiO2 /γ-Fe2 O3 -immobilized palladium complexes. It was characterized by inductively coupled plasma (ICP) analysis, transmission electron microscopy (TEM), scanning transmission electron microscopy (STEM), energy-dispersive X-ray spectroscopy (EDX), and X-ray photoelectron spectra (XPS) and found to fulfill the combined conditions for the selective oxidation of alcohols to aldehydes and ketones.

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Section: Introductionmentioning

confidence: 99%

A Tris(triazolate) Ligand for a Highly Active and Magnetically Recoverable Palladium Catalyst of Selective Alcohol Oxidation Using Air at Atmospheric Pressure

Wang

Deraedt

Salmon

et al. 2015

Chemistry A European J

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“…Oxidation of benzoin is a practically important reaction for the production of benzil or benzaldehyde required in the perfumery and pharmaceutical industries [12][13][14][15][16][17]. Few heterogeneous catalytic methods have been developed for the oxidation of ethylbenzene, benzoin and cyclohexanol [18][19][20][21][22][23].…”

Section: Introductionmentioning

confidence: 99%

Zeolite encapsulated Ru(III), Cu(II) and Zn(II) complexes of benzimidazole as reusable catalysts for the oxidation of organic substrates

Bhagya

Gayathri

2013

J Porous Mater

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Ru(III), Cu(II) and Zn(II) complexes of benzimidazole (BzlH) have been synthesized in the supercages of zeolite-Y by the flexible ligand method and were characterized by spectroscopic (IR, UV-Vis and ESR) studies, XRD and thermogravimetric analysis, surface area, and pore volume measurements. The zeolite encapsulated complexes catalyzed the oxidation of ethylbenzene, benzoin, and cyclohexanol. Various parameters, such as concentration of oxidant and catalyst, reaction time, temperature of the reaction and type of solvents have been optimized to obtain the maximum transformation of ethylbenzene to a mixture of acetophenone, benzaldehyde and styrene. Under the optimized reaction conditions, [Ru(BzlH)]-Y gave 80.4 % conversion of ethylbenzene in 1 h. All these zeolite encapsulated complexes were more selective towards acetophenone formation. Oxidation of benzoin catalyzed by [Cu(BzlH)]-Y, [Ru(BzlH)]-Y and [Zn(BzlH)]-Y encapsulated complexes resulted in 75.5, 78.7 and 59.9 % conversion respectively to give benzaldehyde as exclusive product. A maximum conversion of 39.1 % cyclohexanol with [Cu(BzlH)]-Y was achieved to give cyclohexanone. The activity of neat complexes towards these reactions was also carried out. The encapsulated catalysts were significantly more active than neat complexes and recyclable without much loss in catalytic activity.

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“…1,2-Diketones have been synthesized with different reagents, such as oxidation of 1,2-diols [37,38], oxidation of alkynes [39][40][41][42][43][44][45][46][47][48][49], oxidation of alkenes [50], oxidation of a-methylene ketones [51], rearrangement of a,b-epoxyketones [52][53][54], oxidation of vicinal dihaloalkenes [55], oxidation of epoxides [56], oxidation of 1,3-diols [57], and oxidation with molecular oxygen. They have been catalyzed by trichlorooxyvanadium [58], nickel-aluminum hydrotalcite [59], and chiral cobalt complex [60], while palladium-catalyzed oxidation of benzoins to benzils was achieved by using CsOH or K 2 CO 3 as a base [61][62][63]. Porphyrins and metalloporphyrin complexes have been used in numerous biological systems [64].…”

Section: Introductionmentioning

confidence: 99%

Oxidation of benzoins to benzils in the presence of porphyrin sensitizers by air and sunlight or visible light

et al. 2013

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In this work, two new aerobic routes are introduced for the oxidation of a variety of benzoins to benzils by using molecular oxygen in the presence of porphyrins as sensitizers, using white light or sunlight in acetonitrile under mild conditions. The methods have a wide range of applications, do not involve cumbersome work-up, exhibit chemoselectivity and proceed under mild reaction conditions. The resulting products are obtained in good yields in a reasonable time.

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Aerobic oxidation of α-hydroxycarbonyls catalysed by trichlorooxyvanadium: efficient synthesis of α-dicarbonyl compounds

Cited by 129 publications

References 8 publications

A Tris(triazolate) Ligand for a Highly Active and Magnetically Recoverable Palladium Catalyst of Selective Alcohol Oxidation Using Air at Atmospheric Pressure

A Tris(triazolate) Ligand for a Highly Active and Magnetically Recoverable Palladium Catalyst of Selective Alcohol Oxidation Using Air at Atmospheric Pressure

Zeolite encapsulated Ru(III), Cu(II) and Zn(II) complexes of benzimidazole as reusable catalysts for the oxidation of organic substrates

Oxidation of benzoins to benzils in the presence of porphyrin sensitizers by air and sunlight or visible light

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