A Mild Catalytic Oxidation System: FePcOTf/H2O2 Applied for Cyclohexene Dihydroxylation

Zhou, Bingwei

doi:10.3390/molecules20058429

Cited by 6 publications

(4 citation statements)

References 44 publications

(57 reference statements)

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“…As a result, recent decade witnesses a great number of reports about MPc especially their applications as catalysts. Fe(II)-Pc is an active MPc that was employed in the oxidation of wide variety of organic substrates including β -isophorone 4 , catechol 5 , starch 6 , aromatic pollutant 7 , cyclohexene 8 , cyclohexane 9 , alcohols 10 , and methane 11 . The high activity of this catalyst is attributed to the large number of π electrons which are easily transported between the catalyst and substrate, similar to its analogue, Fe(II)-porphyrin 12 .…”

Section: Introductionmentioning

confidence: 99%

Fe(II)-phthalocyanine supported on chitosan aerogel as a catalyst for oxidation of alcohols and alkyl arenes

Azimi

Marjani

Keshipour

2021

Sci Rep

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Manipulation of materials is considered as one of the eminent strategies to create desirable catalysts. In this regard, increasing surface area and decreasing dimensions of catalysts have been widely employed on account of effectiveness of these methods. Herein, aerogel form of chitosan as a sustainable, and high aspect ratio compound is employed as a green support for the catalytic purposes. Chitosan aerogel was modified with Fe(II)-phthalocyanine to produce a heterogeneous catalyst for oxidation reactions. The synthesized catalyst promoted the oxidation reactions of alcohols and alkyl arenes to the corresponding aldehydes and ketones using H2O2 as an oxidant in 24 h. The reactions for aliphatic and aromatic alcohols gave turnover numbers of 106–109 at 80 °C and 106–117 at room temperature, respectively. The oxidations of alkyl arenes were carried out with turnover numbers laying in the range of 106–117 at 100 °C. The low toxicity, inexpensive nature, and recycling possibility of the catalyst accompanied by the reaction mild conditions, clean oxidant, and excellent yields offer chitosan aerogel modified with Fe(II)-phthalocyanine as a promising catalyst for oxidation reactions.

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Section: Introductionmentioning

confidence: 99%

Fe(II)-phthalocyanine supported on chitosan aerogel as a catalyst for oxidation of alcohols and alkyl arenes

Azimi

Marjani

Keshipour

2021

Sci Rep

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“…To overcome this obstacle, organic initiators (generally peroxides, peracids, diazo-compounds, etc. ) , and/or promoters (e.g., aliphatic aldehydes) are usually explored. , According to the mechanism, the enlisted compounds speed up the oxidation using the free radicals generated in the course of their homolysis. In a similar, although not identical, manner, N -hydroxyphthalimide (NHPI) , enables to transfer electrons by the way of mimicking biological oxidation. , …”

Section: Introductionmentioning

confidence: 99%

“…10 To overcome this obstacle, organic initiators (generally peroxides, peracids, diazo-compounds, etc.) 12,13 and/or promoters (e.g., aliphatic aldehydes) are usually explored. 14,15 According to the mechanism, the enlisted compounds speed up the oxidation using the free radicals generated in the course of their homolysis.…”

Section: Introductionmentioning

confidence: 99%

Sustainable Oxidation of Cyclohexane and Toluene in the Presence of Affordable Catalysts: Impact of the Tandem of Promoter/Oxidant on Process Efficiency

Pokutsa¹,

Tkach²,

Zaborovskyi³

et al. 2020

ACS Omega

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The oxygenation of cyclohexane and toluene by O2 and H2O2 catalyzed by VO(acac)2 and Co(acac)2 was studied at 40–100 °C and 1–10 atm. Upon such conditions, the process can be remarkably (30× times) enhanced by the minute (6–15 mM) additives of oxalic acid (OxalH) or N-hydroxyphthalimide (NHPI). The revealed effect of OxalH on H2O2-piloted oxidation is closely associated with the nature of the catalyst cation and boosted by VO(acac)2. Whereas the effectiveness of Co(acac)2-based systems was curbed by the addition of OxalH and remained much below the one displayed with the previous system. The observed conspicuous difference in activity was attributed to the substantially higher solubility of in situ formed VO(IV)oxalate compared to that of Co(II)oxalate. The exploration of H2O2 for the NHPI-promoted process leads to the decisively lower (5–7 times) yield in comparison to the O2-driven reaction. Similarly, for the O2-operated protocol, the yield cannot be improved by addition of OxalH either to VO(acac)2 + NHPI or to Co(acac)2 + NHPI mixture. By contrast, the combination of NHPI with VO(acac)2 or Co(acac)2 and particularly with the above two mixtures in O2-piloted oxidation enhances the yield of the aimed products 3–6 times regardless of the substrate used. The revealed significant synergetic effect of the cobalt + vanadyl bicomponent catalyst was due to the participation of each of its moiety in the different stages of the process mechanism. Only benzyl alcohol and benzaldehyde were identified in VO(acac)2- or Co(acac)2-catalyzed toluene oxidation, while cyclohexane oxidation yields cyclohexylhydroperoxide in line with cyclohexanol and cyclohexanone. The putative mechanism of investigated processes is highlighted and discussed.

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“…It was found that the catalyst FePcOTf shows excellent conversion and moderate selectivity relative to other iron(III) phthalocyanine complexes. 187 Simple Fe(NO 3 ) 3 •9H 2 O was demonstrated to be able to catalyze the oxidation of monoterpenes by hydrogen peroxide in methanol. In these reactions, α-and β-pinene were preferentially oxidized to allylic ethers (i.e., myrtenol methyl ether).…”

Section: Epoxidationmentioning

confidence: 99%

Synthetic utility of metal catalyzed hydrogen peroxide oxidation of C-H, C-C and C=C bonds in alkanes, arenes and alkenes: Recent advances

Wójtowicz‐Młochowska¹

2016

Arkivoc

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This review presents the current state of the art of homogenic and heterogenic oxygen transfer processes using hydrogen peroxide as oxygen source and compounds and complexes of tranisition metals, Fe, V, Cu, Mn, Rh, Mo, Ti, W, Pd, Os, Zr, Cr, Nb, Co, as the catalysts. Based on the reactions of C-H, C-C and C=C bonds in alkanes, arenes and alkenes various mechanisms of the oxygen-transfer processes are discussed and new methodologies for synthesis of alcohols, phenols, aldehydes, ketones, epoxides and carboxylic acids are indicated.

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A Mild Catalytic Oxidation System: FePcOTf/H2O2 Applied for Cyclohexene Dihydroxylation

Cited by 6 publications

References 44 publications

Fe(II)-phthalocyanine supported on chitosan aerogel as a catalyst for oxidation of alcohols and alkyl arenes

Fe(II)-phthalocyanine supported on chitosan aerogel as a catalyst for oxidation of alcohols and alkyl arenes

Sustainable Oxidation of Cyclohexane and Toluene in the Presence of Affordable Catalysts: Impact of the Tandem of Promoter/Oxidant on Process Efficiency

Synthetic utility of metal catalyzed hydrogen peroxide oxidation of C-H, C-C and C=C bonds in alkanes, arenes and alkenes: Recent advances

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