Asymmetric oxidation of sulfides by hydrogen peroxide catalyzed by chiral manganese porphyrins in water/methanol solution

Srour, Hassan; Jalkh, Joanna; Maux, Paul Le; Chevance, Soizic; Kobeissi, Marwan; Simonneaux, Gérard

doi:10.1016/j.molcata.2012.12.016

Cited by 40 publications

(15 citation statements)

References 35 publications

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“…Another example of an enantioselective oxidation of sulfides (small scale) catalysed by a chiral manganese porphyrin in an aqueous methanol solution in the presence of H 2 O 2 furnished the non-steroidal anti-inflammatory drug Sulindac ® (Banyu Pharmaceutical Co., Ltd., Tokyo, Japan) (Scheme 10b) [57].…”

Section: Sulfides To Sulfoxidesmentioning

confidence: 99%

“…The use of oxygen as the oxidant with NaBH 4 and Me 4 NOH, [58] is an example to obtain the oxidized product of diarylsulfide compounds (Scheme 11). non-steroidal anti-inflammatory drug Sulindac ® (Banyu Pharmaceutical Co., Ltd., Tokyo, Japan) (Scheme 10b) [57]. Nonetheless, the formation of sulfoxides using metalloporphyrins as catalyst can be achieved by other methodologies, but in this case, on a superior scale.…”

Section: Sulfides To Sulfoxidesmentioning

confidence: 99%

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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: Sulfides To Sulfoxidesmentioning

confidence: 99%

Section: Sulfides To Sulfoxidesmentioning

confidence: 99%

Porphyrins as Catalysts in Scalable Organic Reactions

et al. 2016

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“…[144][145][146][147][148] Research efforts towards developing viable and environmentally benign synthetic methodologies for oxidation of organic sulfides to sulfoxides and sulfones appear to have intensified, in recent times. [149][150][151] We could achieve clean conversion to high purity sulfoxide or sulfone from the corresponding sulfides as well as dibenzothiophene (DBT), in presence of catalytic amounts of the compounds MRVMo or MRAMo in impressive yields and TOF, by establishing appropriate reaction conditions.…”

Section: Catalytic Activity In Sulfide Oxidationmentioning

confidence: 99%

Macromolecular peroxo complexes of Vanadium(V) and Molybdenum(VI): Catalytic activities and biochemical relevance

Islam

Boruah

2015

J Chem Sci

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Our recent achievements concerning the synthesis and characterization of water soluble peroxo complexes of V(V) and Mo(VI) in macroligand environment, as well as some key features of biological relevance of these compounds, such as their hydrolytic stability, activity with phosphohydrolase enzyme vis-à-vis free peroxovanadium (pV) or peroxomolybdenum (pMo) complexes, and their activity in biomimetic oxidative bromination are presented here. Immobilization of pMo species on insoluble polymer matrices viz., amino acid functionalized Merrifield resins and poly(acrylonitrile) on the other hand, afforded a set of heterogeneous catalysts highly effective in facile organic transformations such as selective oxidation of organic sulfides and oxidative bromination of aromatic substrates by H 2 O 2 , at ambient temperature. The methodologies are straightforward, high-yielding, halogen-free and the catalysts afford easy regeneration. Our findings illustrate the various features which make the procedures sustainable and synthetically useful.

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“…A similar effect was found for the oxidation of sulfides. The proposed procedure requires an aqueous medium and the presence of imidazole as a catalyst [153].…”

Section: Article In Pressmentioning

confidence: 99%