Metal-Catalyzed Epoxidations of Alkenes with Hydrogen Peroxide

Lane, Benjamin S.; Burgess, Kevin

doi:10.1021/cr020471z

Cited by 1,105 publications

(479 citation statements)

References 189 publications

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“…Dissolution of the oil in pentane followed by cooling to − 115 °C separated 1 H in a pure form. 1 4 ]PF 6 in a 200 mL Schlenk flask under N 2 . Approximately 150 mL of MeCN were added to form a deep brown solution before the addition of 7.5 g of SBA-15.…”

Section: Ligand Synthesesmentioning

confidence: 99%

Covalent Heterogenization of a Discrete Mn(II) Bis-Phen Complex by a Metal-Template/Metal-Exchange Method: An Epoxidation Catalyst with Enhanced Reactivity

and

Stack

2008

J. Am. Chem. Soc.

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Considerable attention has been devoted to the immobilization of discrete epoxidation catalysts onto solid supports due to the possible benefits of site isolation such as increased catalyst stability, catalyst recycling, and product separation. A synthetic metal-template/metal-exchange method to imprint a covalently attached bis-1,10-phenanthroline coordination environment onto high-surface area, mesoporous SBA-15 silica is reported herein along with the epoxidation reactivity once reloaded with manganese. Comparisons of this imprinted material with material synthesized by random grafting of the ligand show that the template method creates more reproducible, solution-like bis-1,10-phenanthroline coordination at a variety of ligand loadings. Olefin epoxidation with peracetic acid shows the imprinted manganese catalysts have improved product selectivity for epoxides, greater substrate scope, more efficient use of oxidant, and higher reactivity than their homogeneous or grafted analogues independent of ligand loading. The randomly grafted manganese catalysts, however, show reactivity that varies with ligand loading while the homogeneous analogue degrades trisubstituted olefins and produces trans-epoxide products from cis-olefins. Efficient recycling behavior of the templated catalysts is also possible.

show abstract

Section: Ligand Synthesesmentioning

confidence: 99%

Covalent Heterogenization of a Discrete Mn(II) Bis-Phen Complex by a Metal-Template/Metal-Exchange Method: An Epoxidation Catalyst with Enhanced Reactivity

and

Stack

2008

J. Am. Chem. Soc.

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show abstract

“…In fact, during the last decades the oxidation of organic compounds with hydrogen peroxide catalysed by metals has focussed considerable attention as a feasible alternative to environmentally harmful oxidants [1,2]. Hydrogen peroxide is a clean oxidant, although, often, some problems arise associated to its use, such as decomposition, thus losing "oxidative capacity" [3].…”

Section: Introductionmentioning

confidence: 99%

Influence of peroxometallic intermediaries present on polyoxometalates nanoparticles surface on the adipic acid synthesis

Alcañiz-Monge

Trautwein

Garcı́a-Garcı́a

2014

Journal of Molecular Catalysis A: Chemical

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“…The epoxidation of olefin is one of the most important reactions for both bulk and fine chemicals [1,2]. After pioneering works using Ti-zeolites such as TS-1 [3], mesoporous mixed oxide catalysts with larger pores (e.g., Ti substituted mesoporous silica) were developed to expand its applicability to this reaction [4][5][6][7][8][9][10].…”

Section: Introductionmentioning

confidence: 99%

Remarkable effect of ordered mesoporous carbon support in tantalum oxide-catalyzed selective epoxidation of cyclooctene

Lin

Hara

Okubo

et al. 2011

Catalysis Communications

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The olefin epoxidation is one of the most important reactions in chemical industry. Metal oxide supports often cause drawbacks in catalytic activity and selectivity, which has been overcome by introducing hydrophobic organic groups onto the oxide supports. The present study utilizes ordered mesoporous carbon (CMK-3 and CMK-1) as structurally defined hydrophobic catalyst support. Well-dispersed tantalum oxides supported on the ordered mesoporous carbon were prepared. Their application in catalytic epoxidation of cyclooctene demonstrates that the tantalum oxide catalysts on the ordered mesoporous carbon supports show higher performances than those of the catalysts supported on activated carbon and ordered mesoporous silica SBA-15.

show abstract

Metal-Catalyzed Epoxidations of Alkenes with Hydrogen Peroxide

Cited by 1,105 publications

References 189 publications

Covalent Heterogenization of a Discrete Mn(II) Bis-Phen Complex by a Metal-Template/Metal-Exchange Method: An Epoxidation Catalyst with Enhanced Reactivity

Covalent Heterogenization of a Discrete Mn(II) Bis-Phen Complex by a Metal-Template/Metal-Exchange Method: An Epoxidation Catalyst with Enhanced Reactivity

Influence of peroxometallic intermediaries present on polyoxometalates nanoparticles surface on the adipic acid synthesis

Remarkable effect of ordered mesoporous carbon support in tantalum oxide-catalyzed selective epoxidation of cyclooctene

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