Melamine Hydrogen Peroxide (MHP): Novel and Efficient Reagent for the Chemo- and Homoselective and Transition Metal–Free Oxidation of Thiols and Sulfides

Chehardoli, Gholamabbas; Zolfigol, Mohammad Ali

doi:10.1080/10426500902758386

Cited by 37 publications

(22 citation statements)

References 51 publications

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“…Its crystals are composed of molecules of urea and hydrogen peroxide in 1:1 ratio, connected through multiple hydrogen bonds [13]. Hydrogen peroxide forms also complexes with melamine [14] and DABCO-di-N-oxide [15]. Some polymer-supported systems containing hydrogen peroxide are known as well.…”

Section: Introductionmentioning

confidence: 99%

Adsorption of hydrogen peroxide on functionalized mesoporous silica surfaces

2014

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MCM-41 and MSU-H mesoporous silicas were successfully functionalized with hydrogen bonds forming organic moieties, which have been proven by elemental analysis. Both moieties, based on oxygen and nitrogen containing groups, were introduced with high efficiencythe amount of carbon in all cases exceeded 10 % and the elemental ratios suggest binding to the surface through two or three Si-O-Si bonds. Hydrogen peroxide adsorption was conducted in its aqueous solutions and the amount adsorbed was determined using the ferric thiocyanate method. Results are presented as a function of hydrogen peroxide concentration in aqueous solution from 5 to 30 %. Both functionalized silicas show increased adsorption capacity when compared with that of their unfunctionalized analogues. The surface modified with nitrogen-based organic moiety revealed better adsorption properties as well as higher resistance against oxidation. MSU-H silica, due to its larger pore diameter, provides more space to bind hydrogen peroxide molecules and thus was found to have higher adsorption capacity: it adsorbed up to four times more hydrogen peroxide than MCM-41.

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Section: Introductionmentioning

confidence: 99%

Adsorption of hydrogen peroxide on functionalized mesoporous silica surfaces

2014

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“…When there are two or more identical functional groups in a molecule, only one of them reacts selectively during the reaction; this selectivity can be named homoselectivity . It is notable that these oxidizing systems homoselectively oxidized 2,2′‐disulfanediyldibenzoic acid to its monosulfoxide derivative without further oxidation to disulfoxide or sulfone (Table , entries 11; Scheme ).…”

Section: Resultsmentioning

confidence: 99%

“…When there are two or more identical functional groups in a molecule, only one of them reacts selectively during the reaction; this selectivity can be named homoselectivity. [48,49] It is notable that these oxidizing systems homoselectively oxidized 2,2′-disulfanediyldibenzoic acid to its monosulfoxide derivative without further oxidation to disulfoxide or sulfone ( reaction was finished, the catalyst was isolated, washed with ethyl acetate and recycled. It was observed that the catalyst retained excellent action for a minimum of seven runs (Figure 12).…”

Section: Chemo-and Homoselective Oxidation Of Sulfidesmentioning

confidence: 99%

Immobilization of cerium (IV) and erbium (III) in mesoporous MCM‐41: Two novel and highly active heterogeneous catalysts for the synthesis of 5‐substituted tetrazoles, and chemo‐ and homoselective oxidation of sulfides

Molaei

Ghadermazi

2019

Applied Organom Chemis

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Two well‐ordered 2D‐hexagonal cerium (IV) and erbium (III) embedded functionalized mesoporous MCM‐41(MCM‐41@Serine/Ce and MCM‐41@Serine/Er) have been developed via functionalization of mesoporous MCM‐41. The surface modification method has been used in the preparation of serine‐grafted MCM‐41 and led to the development of MCM‐41@Serine. The reaction of MCM‐41@Serine with Ce (NH4)2(NO3)6·2H2O or ErCl3·6H2O in ethanol under reflux led to the organization of MCM‐41@Serine/Ce and MCM‐41@Serine/Er catalysts. The structures of these catalysts were determined using scanning electron microscopy, mapping, energy‐dispersive X‐ray spectroscopy, Fourier transform‐infrared, thermogravimetric analysis, X‐ray diffraction, inductively coupled plasma, and Brunauer–Emmett–Teller analysis. These MCM‐41@Serine/Ce and MCM‐41@Serine/Er catalysts show outstanding catalytic performance in sulfides oxidation and synthesis of 5‐substituted tetrazoles. These catalysts can be recycled for seven repeated reaction runs without showing a considerable decrease in catalytic performance.

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“…For example, many methods have been reported in the presence of various catalysts and using different oxidant (e.g. metal oxidants, organic oxidant, peroxides, halogens, and air) [33] [35,36], melamine hydrogen peroxide [37] and urea hydrogen peroxide [38] have been used as oxidant for oxidation of sulfides and oxidative coupling of thioles previously. Concerning the green oxidant, H 2 O 2 (with only H 2 O as a byproduct) in particular have received attention because of their environmental implications, readily available, high atom efficiency and lower costs than when used other oxidizing agents [39].…”

Section: Introductionmentioning

confidence: 99%

Schiff base complex of Cu immobilized on MCM-41 as reusable catalyst for efficient oxidative coupling of thiols and oxidation of sulfides using hydrogen peroxide

Hajjami

Rahmani

2015

J Porous Mater

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Schiff base complex of copper-functionalized ) was synthesized and used as an efficient and novel heterogeneous catalyst for the oxidative coupling of thiols into corresponding disulfides and oxidation of sulfides to sulfoxides using hydrogen peroxide (H 2 O 2 ) as the oxidant. An aliphatic and aromatic series of sulfides and thiols including various functional groups were successfully converted into corresponding products. The all products were obtained in good to excellent yields. The mesoporous catalyst is characterized by FT-IR spectroscopy, BET, XRD, SEM, EDS and TGA. Recovery of the catalyst is easily achieved by simple filtration and reused for several consecutive runs without significant loss of its catalytic efficiency.

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Melamine Hydrogen Peroxide (MHP): Novel and Efficient Reagent for the Chemo- and Homoselective and Transition Metal–Free Oxidation of Thiols and Sulfides

Cited by 37 publications

References 51 publications

Adsorption of hydrogen peroxide on functionalized mesoporous silica surfaces

Adsorption of hydrogen peroxide on functionalized mesoporous silica surfaces

Immobilization of cerium (IV) and erbium (III) in mesoporous MCM‐41: Two novel and highly active heterogeneous catalysts for the synthesis of 5‐substituted tetrazoles, and chemo‐ and homoselective oxidation of sulfides

Schiff base complex of Cu immobilized on MCM-41 as reusable catalyst for efficient oxidative coupling of thiols and oxidation of sulfides using hydrogen peroxide

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