An Efficient Oxidation of Alcohols by Aqueous H2O2 with 1,3-Dibromo- 5,5-Dimethylhydantoin

Lee, Jieun; Lee, Jong Chan

doi:10.2174/1570178615666180613080548

Cited by 6 publications

(3 citation statements)

References 22 publications

(22 reference statements)

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“…The oxidation of alcohol is one of the most important reactions in the synthesis of organic compounds. [30][31][32][33][34][35][36][37][38] Some of these reactions occur under difficult conditions, such as high temperatures, the use of unfavorable solvents, and the use of toxic oxidizing agents, including transition metal compounds that produce harmful byproducts. Usually, compounds such as chromic acid, di- Tabari et al: Magnetic Nanoparticles Linked ... chromate/H + , PCC, PDC are used to oxidize alcohols.…”

Section: Resultsmentioning

confidence: 99%

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Magnetic Nanoparticles Linked to Pyridinium Hydrotribromide Groups as Catalysts for Selective Oxidation of Alcohols and Protection of Alcohols

Tabari

Pourali

Zare

2022

ACSi

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In this research, a novel magnetic nanocatalyst based on iron oxide nanoparticles linked with pyridinium hydrotribromide (Fe3O4@PyHBr3) was synthesized in three steps. In the first step, 3-(aminopropyl)triethoxysilane (APTES) was reacted with 4-(bromomethyl)pyridine hydrobromide. In the second step, the product obtained in the first step was reacted with iron oxide nanoparticles. In the last step, a grinding reaction was carried out with KBr and HIO4 in a mortar. The Fe3O4@PyHBr3 nanocatalyst was characterized by FT-IR, CHN, XRD, SEM, TGA and VSM analysis. The magnetic nanocatalyst was used as a catalyst for the selective oxidation of alcohols to aldehydes and ketones using 30% H2O2 as oxidant in a short time and with high yields. Moreover, no overoxidation of the alcohols was observed. The nanocatalyst was efficiently recycled in five consecutive cycles without significant loss of its catalytic activity. Moreover, trimethylsilylation and tetrahydropyranylation of alcohols were carried out in the presence of this nanocatalyst.

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Section: Resultsmentioning

confidence: 99%

“…Hydrogen peroxide (H 2 O 2 ) is an attractive oxidant for liquid-phase reactions. [34][35][36][37][38] This water-soluble oxidant is safe, inexpensive, and has a high oxygen content that does not require a buffer. In addition, it is considered a green and environmentally friendly oxidant because it releases water as a byproduct.…”

Section: Resultsmentioning

confidence: 99%

Magnetic Nanoparticles Linked to Pyridinium Hydrotribromide Groups as Catalysts for Selective Oxidation of Alcohols and Protection of Alcohols

Tabari

Pourali

Zare

2022

ACSi

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“…Similar to peroxoborate, H 2 O 2 alone has only a low oxidizing capacity with respect to the conversion of primary and secondary alcohols to their corresponding aldehydes and ketones, respectively [ 45 ]. Therefore, in order to enhance this poor oxidation capacity, a range of transition metal ion complexes, such as those of gold, iron, manganese, molybdenum, tungsten, or bismuth has been employed for the oxidation of alcohols, as have selected organic agents such as 1,3-dibromo-5,5-dimethylhydantoin [ 45 ].…”

Section: Differential Reactivities Of Peroxoborate Species and H mentioning

confidence: 99%

Potential Advantages of Peroxoborates and Their Ester Adducts Over Hydrogen Peroxide as Therapeutic Agents in Oral Healthcare Products: Chemical/Biochemical Reactivity Considerations In Vitro, Ex Vivo And In Vivo

et al. 2020

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Peroxides present in oral healthcare products generally exert favourable protective activities against the development and progression of tooth decay, plaque, gingivitis, and halitosis, etc. However, despite the high level of research focus on hydrogen and carbamide peroxides as therapeutically active (and tooth-whitening) agents, to date the use of alternative chemical forms of peroxides such as peroxoborates for these purposes has received only scant attention. Intriguingly, peroxoborate and its esters with polyols, such as glycerol, have a very diverse chemistry/biochemistry in aqueous solution, for which there is an increasing amount of evidence that it remains distinctive from that of hydrogen peroxide; such properties include self-associative and hydrolytic equilibria, and their abilities to participate in electrophile- or nucleophile-scavenging, metal ion-complexing, redox and free radical reactions, for example. Therefore, the purpose of this detailed commentary is to evaluate both differences and similarities between the molecular/biomolecular reactivities of peroxoborate species and hydrogen peroxide in vitro, ex-vivo and in vivo. It encompasses brief sectional accounts regarding the molecular heterogeneity of peroxoborates, the release of bioactive agents therefrom, and their oxidative attack on oral cavity biomolecules (the nucleophilic or electrophilic character of these oxidations are discussed). Further areas explored are the abilities of borates and peroxoborates to enhance the solubility of iron ions in aqueous solution, their involvements in free radical biochemistry (particularly the complexation of oxygen radical-promoting transition metal ions by, and antioxidant properties of, peroxoborate-polyol ester adducts), and the specific inhibition of protease enzymes. Further aspects focus on the tooth-whitening, oral malodor neutralizing, and potential mutagenic and genotoxic properties of peroxoborates, along with possible mechanisms for these processes. The abilities of peroxoborates, and peroxides in general, to modulate the activities of inflammatory mediators and vitamins, antioxidant or otherwise, are also explored.

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Catalytic Selective Oxidation of Primary and Secondary Alcohols Using Nonheme [Iron(III)(Pyridine‐Containing Ligand)] Complexes

et al. 2020

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The selective oxidation of different primary and secondary alcohols to carbonyl compounds by hydrogen peroxide was found to be catalyzed in conversion ranging from good to excellent by an iron(III) complex of a pyridine‐containing macrocyclic ligand (Pc‐L), without the need of any additive. The choice of the counteranion (Cl, Br, OTf) appeared to be of fundamental importance and the best results in terms of selectivity (up to 99 %) and conversion (up to 98 %) were obtained using the well‐characterized [Fe(III)(Br)2(Pc‐L)]Br complex, 4c. Magnetic moments in solid‐state, also confirmed in solution ([D6]DMSO) by Evans NMR method, were calculated and point out to an iron metal center in the high spin state of 5/2. The crystal structure shows that the iron(III) center is coordinated by the four nitrogen atoms of the macrocycle and two bromide anions to form a distorted octahedral coordination environment. The catalytic oxidation of benzyl alcohol in acetonitrile was found occurring with better conversions and selectivities than in other solvents. The reaction proved to be quite general, tolerating aromatic and aliphatic alcohols, although very low yields were obtained for terminal aliphatic alcohols. Preliminary mechanistic studies are in agreement with a catalytic cycle promoted by a high‐spin iron complex.

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An Efficient Oxidation of Alcohols by Aqueous H2O2 with 1,3-Dibromo- 5,5-Dimethylhydantoin

Abstract: An efficient protocol is described for the oxidation of alcohols to the corresponding aldehydes or ketones with 1,3-dibromo-5,5-dimethylhydantoin in the presence of aqueous H2O2.

Cited by 6 publications

References 22 publications

Magnetic Nanoparticles Linked to Pyridinium Hydrotribromide Groups as Catalysts for Selective Oxidation of Alcohols and Protection of Alcohols

Magnetic Nanoparticles Linked to Pyridinium Hydrotribromide Groups as Catalysts for Selective Oxidation of Alcohols and Protection of Alcohols

Potential Advantages of Peroxoborates and Their Ester Adducts Over Hydrogen Peroxide as Therapeutic Agents in Oral Healthcare Products: Chemical/Biochemical Reactivity Considerations In Vitro, Ex Vivo And In Vivo

Catalytic Selective Oxidation of Primary and Secondary Alcohols Using Nonheme [Iron(III)(Pyridine‐Containing Ligand)] Complexes

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