Metal-catalyzed asymmetric sulfoxidation, epoxidation and hydroxylation by hydrogen peroxide

Srour, Hassan; Maux, Paul Le; Chevance, Soizic; Simonneaux, Gérard

doi:10.1016/j.ccr.2013.05.010

Cited by 156 publications

(84 citation statements)

References 206 publications

(243 reference statements)

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“…Oxidation reactions are important synthetic tools, and a number of applications can be found in the chemical industry [24]. The manufacture of products obtained from oxidation of organic substrates and the production of pharmaceutical ingredients (APIs) are of major importance [25].…”

Section: Oxidation Reactions With Porphyrin and Metalloporphyrin-basementioning

confidence: 99%

Porphyrins as Catalysts in Scalable Organic Reactions

et al. 2016

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Catalysis is a topic of continuous interest since it was discovered in chemistry centuries ago. Aiming at the advance of reactions for efficient processes, a number of approaches have been developed over the last 180 years, and more recently, porphyrins occupy an important role in this field. Porphyrins and metalloporphyrins are fascinating compounds which are involved in a number of synthetic transformations of great interest for industry and academy. The aim of this review is to cover the most recent progress in reactions catalysed by porphyrins in scalable procedures, thus presenting the state of the art in reactions of epoxidation, sulfoxidation, oxidation of alcohols to carbonyl compounds and C-H functionalization. In addition, the use of porphyrins as photocatalysts in continuous flow processes is covered.

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Section: Oxidation Reactions With Porphyrin and Metalloporphyrin-basementioning

confidence: 99%

Porphyrins as Catalysts in Scalable Organic Reactions

et al. 2016

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“…This predominance is shared with manganese-salen complexes, mainly due to the success of the Jacobsen-Katsuki epoxidation process. Still, the theoretical study of transition-metal catalyzed epoxidations goes far beyond the two major examples highlighted in this review [100,101]. A brief overview of the state of the art in the theoretical study of other transition metal-catalyzed epoxidations is thus provided here for completeness.…”

Section: Other Epoxidation Catalysts: a Brief Overviewmentioning

confidence: 99%

Strengths, Weaknesses, Opportunities and Threats: Computational Studies of Mn- and Fe-Catalyzed Epoxidations

Teixeira

Cordeiro

2016

Catalysts

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Abstract:The importance of epoxides as synthetic intermediates in a number of highly added-value chemicals, as well as the search for novel and more sustainable chemical processes have brought considerable attention to the catalytic activity of manganese and iron complexes towards the epoxidation of alkenes using non-toxic terminal oxidants. Particular attention has been given to Mn(salen) and Fe(porphyrin) catalysts. While the former attain remarkable enantioselectivity towards the epoxidation of cis-alkenes, the latter also serve as an important model for the behavior of cytochrome P450, thus allowing the exploration of complex biological processes. In this review, a systematic survey of the bibliographical data for the theoretical studies on Mn-and Fe-catalyzed epoxidations is presented. The most interesting patterns and trends are reported and finally analyzed using an evaluation framework similar to the SWOT (Strengths, Weaknesses, Opportunities and Threats) analysis performed in enterprise media, with the ultimate aim to provide an overview of current trends and areas for future exploration.

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“…[12] Several transition metals have been also applied in order to increase activity and selectivity of hydrogen peroxide for sulfide oxidation. [13] Recently, catalytic systems based on tungsten species have been widely applied in combination with H 2 O 2 , owing to high activity and selectivity of tungsten. [14] Noyori and co-workers were the first to use Na 2 WO 4 / H 2 O 2 combination as a homogeneous catalytic system for oxidation reactions.…”

Section: Introductionmentioning

confidence: 99%

Green route for selective gram‐scale oxidation of sulfides using tungstate/triazine‐based ionic liquid immobilized on magnetic nanoparticles as a phase‐transfer heterogeneous catalyst

Hosseini

Tavakolizadeh

Zohreh

et al. 2017

Applied Organom Chemis

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Tungstate ions were successfully loaded onto triazine-based ionic liquid-functionalized magnetic nanoparticles through an anion exchange process. The use of triazine core for creating ionic liquid led to the immobilization of high amounts of WO 4 2− . The resulting catalyst showed high activity and selectivity in the oxidation of sulfides to sulfoxides with H 2 O 2 as a green oxidant at room temperature. In addition, due to the presence of ammonium groups in the catalyst structure, water dispersibility of the catalyst was increased. More important, the catalyst was magnetically recovered and reused for up to six runs without any marked decrease of activity and selectivity. Finally, easy gramscale oxidation of methylphenyl sulfide as well as fast separation of catalyst and product makes the protocol economical and industrially applicable.

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Metal-catalyzed asymmetric sulfoxidation, epoxidation and hydroxylation by hydrogen peroxide

Cited by 156 publications

References 206 publications

Porphyrins as Catalysts in Scalable Organic Reactions

Porphyrins as Catalysts in Scalable Organic Reactions

Strengths, Weaknesses, Opportunities and Threats: Computational Studies of Mn- and Fe-Catalyzed Epoxidations

Green route for selective gram‐scale oxidation of sulfides using tungstate/triazine‐based ionic liquid immobilized on magnetic nanoparticles as a phase‐transfer heterogeneous catalyst

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