Selective oxidation of aromatic compounds with dioxygen and peroxides catalyzed by phthalocyanine supported catalysts

Sorokin, Alexander B.; Mangematin, Stéphane; Pergrale, Corinne

doi:10.1016/s1381-1169(01)00486-1

Cited by 121 publications

(61 citation statements)

References 55 publications

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“…According to Sorokin et al [22], if the reaction proceeded via heterolytic cleavage of the O-O bond, then the reaction with MPPH and the catalyst should give 2-methyl-1-phenyl-2-propanol. On the other hand, homolytic cleavage of the hydroperoxide leads to a radical mechanism yielding acetone, benzyl alcohol, and benzaldehyde as some of the b-scission fragmentation products.…”

Section: Reaction Mechanismmentioning

confidence: 99%

Liquid-phase catalytic oxidation of organic substrates by a recyclable polymer-supported copper(II) complex

Shilpa

Gayathri

2013

Transition Met Chem

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Chloromethylated polystyrene beads crosslinked with 6.5 % divinylbenzene were functionalized with 2-(2 0 -pyridyl) benzimidazole (PBIMH) and on subsequent treatment with Cu(OAc) 2 in methanol gave a polymersupported diacetatobis(2-pyridylbenzimidazole)copper(II) complex [PS-(PBIM) 2 Cu(II)], which was characterized by physicochemical techniques. The supported complex showed excellent catalytic activity toward the oxidation of industrially important organic compounds such as phenol, benzyl alcohol, cyclohexanol, styrene, and ethylbenzene. An effective catalytic protocol was developed by varying reaction parameters such as the catalyst and substrate concentrations, reaction time, temperature, and substrateto-oxidant ratio to obtain maximum selectivity with high yields of products. Possible reaction mechanisms were worked out. The catalyst could be recycled five times without any metal leaching or much loss in activity. This catalyst is truly heterogeneous and allows for easy work up, as well as recyclability and excellent product yields under mild conditions.

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Section: Reaction Mechanismmentioning

confidence: 99%

Liquid-phase catalytic oxidation of organic substrates by a recyclable polymer-supported copper(II) complex

Shilpa

Gayathri

2013

Transition Met Chem

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“…The oxidation of phenol under the optimized reaction conditions was also carried out using methyl-1-phenyl-2-propyl hydroperoxide (MPPH) as a mechanistic probe, to check for the homolytic versus heterolytic scission of the peroxide O-O bond. According to Sorokin et al [31], if the reaction proceeds via heterolytic cleavage of the O-O bond, then the reaction with MPPH and the catalyst should give 2-methyl-1-phenyl-2-propanol. On the other hand, homolytic cleavage of the hydroperoxide leads to a radical mechanism yielding acetone, benzyl alcohol and benzaldehyde as some of the b-scission products.…”

Section: Reaction Mechanismmentioning

confidence: 99%

A polymer-supported diacetatobis(2-quinolylbenzimidazole)copper(II) complex as an efficient catalyst for oxidation of alcohols with tert-butyl hydroperoxide

Shilpa

Gayathri

2012

Transition Met Chem

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A polymer-supported diacetatobis(2-quinolylbenzimidazole)copper(II) complex [PS-(QBIM) 2 Cu(II)] was synthesized by functionalization of chloromethylated polystyrene cross-linked with 6.5 % divinyl benzene with 2-(2 0 -quinolyl)benzimidazole and subsequent treatment with Cu(OAc) 2 in methanol. The complex was characterized by physical, analytical and spectroscopic techniques. Electronic and ESR spectra, together with magnetic susceptibility measurements, indicated that the complex was paramagnetic with distorted octahedral geometry around the copper. The complex was found to be active toward oxidation of various alcohols including phenol, benzyl alcohol and cyclohexanol using 70 % aqueous tert-butyl hydroperoxide under mild conditions. Under the optimized reaction conditions, cyclohexanol gave 100 % conversion to cyclohexanone, benzyl alcohol gave 98 % yield of benzaldehyde and phenol gave 89 % yield of catechol and 4 % of hydroquinone. The complex was recycled five times without much loss in catalytic activity.

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“…However, before our work, they have never been evoked as the catalysts for the oxidation or other reactions. It is quite surprising because we [18][19][20][21][22][23] and others [23][24][25][26][27] demonstrated promising catalytic properties of µ-oxo diiron phthalocyanines in oxidation. It should be noted that µ-nitrido dimers with unsubstituted phthalocyanine ligands are practically insoluble in most organic solvents and only poorly soluble in 1-chloronaphthalene or pyridine.…”

Section: Introductionmentioning

confidence: 96%

µ-Nitrido Bridged Diiron Phthalocyanines: Old Complexes for New Catalytic Applications

Kudrik¹,

Sorokin²

2011

MHC

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Selective oxidation of aromatic compounds with dioxygen and peroxides catalyzed by phthalocyanine supported catalysts

Cited by 121 publications

References 55 publications

Liquid-phase catalytic oxidation of organic substrates by a recyclable polymer-supported copper(II) complex

Liquid-phase catalytic oxidation of organic substrates by a recyclable polymer-supported copper(II) complex

A polymer-supported diacetatobis(2-quinolylbenzimidazole)copper(II) complex as an efficient catalyst for oxidation of alcohols with tert-butyl hydroperoxide

µ-Nitrido Bridged Diiron Phthalocyanines: Old Complexes for New Catalytic Applications

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