Selective aerobic oxidation of sulfides to sulfoxides catalyzed by coenzyme NAD+ models

Xu, Hua‐Jian; Lin, Yi‐Cheng; Wan, Xin; Yang, Chenxi; Feng, Yi‐Si

doi:10.1016/j.tet.2010.09.076

Cited by 18 publications

(4 citation statements)

References 61 publications

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“…In addition, oxidative desulfurization is a promising method for the removal of some thiophenic sulfur compounds that are not effectively removed from fuels by hydrodesulfurization . There are many catalytic systems for the selective oxidation of sulfides using activated oxidants such as organic hydroperoxides and hydrogen peroxide (H 2 O 2 ) − or O 2 in combination with reductants − and photoirradiation. − In particular, high activity (tens of thousands of turnover numbers (TONs) in some cases), excellent chemo- and enantioselectivity, and broad substrate scope can be achieved for the sulfoxidation with tert -butyl hydroperoxide and H 2 O 2 in the presence of transition metal catalysts such as Ti, V, Mn, Fe, W, and Re. − On the other hand, examples of catalytic oxidation of inactive aryl sulfides with O 2 as the sole oxidant without the need for additives are still limited. − Ce- and Pd-based homogeneous systems promote the sulfoxidation under mild reaction conditions; however, the catalyst/product separation and reuse of the catalysts are very difficult. In addition, heterogeneous systems have several drawbacks, such as low applicability, activity, and selectivity, and requirements of high reaction temperatures, additives, or specific solvents to achieve high catalytic performance (see Table S1).…”

Section: Introductionmentioning

confidence: 99%

Heterogeneously Catalyzed Aerobic Oxidation of Sulfides with a BaRuO₃ Nanoperovskite

Kamata

Sugahara

Kato

et al. 2018

ACS Appl. Mater. Interfaces

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A rhombohedral BaRuO nanoperovskite, which was synthesized by the sol-gel method using malic acid, could act as an efficient heterogeneous catalyst for the selective oxidation of various aromatic and aliphatic sulfides with molecular oxygen as the sole oxidant. BaRuO showed much higher catalytic activities than other catalysts, including ruthenium-based perovskite oxides, under mild reaction conditions. The catalyst could be recovered by simple filtration and reused several times without obvious loss of its high catalytic performance. The catalyst effect, O-labeling experiments, and kinetic and mechanistic studies showed that substrate oxidation proceeds with oxygen species caused by the solid. The crystal structure of ruthenium-based oxides is crucial to control the nature of the oxygen atoms and significantly affects their oxygen transfer reactivity. Density functional theory calculations revealed that the face-sharing octahedra in BaRuO likely are possible active sites in the present oxidation in sharp contrast to the corner-sharing octahedra in SrRuO, CaRuO, and RuO. The superior oxygen transfer ability of BaRuO is also applicable to the quantitative conversion of dibenzothiophene into the corresponding sulfone and gram-scale oxidation of 4-methoxy thioanisole, in which 1.20 g (71% yield) of the analytically pure sulfoxide could be isolated.

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Section: Introductionmentioning

confidence: 99%

Heterogeneously Catalyzed Aerobic Oxidation of Sulfides with a BaRuO₃ Nanoperovskite

Kamata

Sugahara

Kato

et al. 2018

ACS Appl. Mater. Interfaces

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“…[12,13] Previously, aerobic photooxidation of sulfides has been successfully accomplished by using metal complexes or organic dyes as PSs. Noteworthy systemsr eported recently used photosensitizers based on tetra-O-acetyl riboflavin, [2,9] Rose Bengal, [14] thioxanthones, [15] Pt II complexes, [16] Ru II Cu II complexes, [17] coenzyme NAD + , [18] and BODIPY dyes. [19] However,a sf ar as we know,I r III complexes have not been used in similars tudies and, furthermore, improvements can still be made in the field to shorten reactiont imes, enhance the photostability and recyclability of PSs, optimize the selectivity of the reaction, expandt he substrate scope, and avoid organic solvents and UV light.…”

Section: Introductionmentioning

confidence: 99%

Selective Photooxidation of Sulfides Catalyzed by Bis‐cyclometalated Ir^III Photosensitizers Bearing 2,2′‐Dipyridylamine‐Based Ligands

Vaquero

Ruiz-Riaguas

Martı́nez-Alonso

et al. 2018

Chemistry A European J

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A new family of heteroleptic bis-cyclometalated Ir complexes with formula [Ir(CN^ ) (NN^ )]Cl (CN^ =2-phenylpyridinate and NN^ =2,2'-dipyridylamine or N-benzylated 2,2'-dipyridylamines, were synthesized, characterized, and successfully used as photosensitizers in the catalytic photooxidation of an array of dialkyl, dibenzyl, alkyl aryl, and diaryl sulfides, as well as sulfur-containing amino acids. Furthermore, the reactions proceeded with optimal chemoselectivity, and atom economy under mild conditions. Experimental observations support a dual mechanism in which singlet oxygen and superoxide are the actual oxidants.

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“…Despite their wide employment, − their separation is very difficult due to the homogeneous reaction system. Recently, to address this problem effort has been focused mainly on loading the homogeneous catalyst on some solid supports .…”

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confidence: 99%

Magnetic Nano-Fe₃O₄-Supported 1-Benzyl-1,4-dihydronicotinamide (BNAH): Synthesis and Application in the Catalytic Reduction of α,β-Epoxy Ketones

Wan

Shen

et al. 2012

Org. Lett.

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A novel magnetically recoverable organic hydride compound was successfully constructed by using silica-coated magnetic nanoparticles as a support. An as-prepared magnetic organic hydride compound, BNAH (1-benzyl-1,4-dihydronicotinamide), showed efficient activity in the catalytic reduction of α,β-epoxy ketones. After reaction, the magnetic nanoparticle-supported BNAH can be separated by simple magnetic separation which made the separation of the product easier.

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Selective aerobic oxidation of sulfides to sulfoxides catalyzed by coenzyme NAD+ models

Cited by 18 publications

References 61 publications

Heterogeneously Catalyzed Aerobic Oxidation of Sulfides with a BaRuO₃ Nanoperovskite

Heterogeneously Catalyzed Aerobic Oxidation of Sulfides with a BaRuO₃ Nanoperovskite

Selective Photooxidation of Sulfides Catalyzed by Bis‐cyclometalated Ir^III Photosensitizers Bearing 2,2′‐Dipyridylamine‐Based Ligands

Magnetic Nano-Fe₃O₄-Supported 1-Benzyl-1,4-dihydronicotinamide (BNAH): Synthesis and Application in the Catalytic Reduction of α,β-Epoxy Ketones

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Selective aerobic oxidation of sulfides to sulfoxides catalyzed by coenzyme NAD+ models

Cited by 18 publications

References 61 publications

Heterogeneously Catalyzed Aerobic Oxidation of Sulfides with a BaRuO3 Nanoperovskite

Heterogeneously Catalyzed Aerobic Oxidation of Sulfides with a BaRuO3 Nanoperovskite

Selective Photooxidation of Sulfides Catalyzed by Bis‐cyclometalated IrIII Photosensitizers Bearing 2,2′‐Dipyridylamine‐Based Ligands

Magnetic Nano-Fe3O4-Supported 1-Benzyl-1,4-dihydronicotinamide (BNAH): Synthesis and Application in the Catalytic Reduction of α,β-Epoxy Ketones

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Heterogeneously Catalyzed Aerobic Oxidation of Sulfides with a BaRuO₃ Nanoperovskite

Heterogeneously Catalyzed Aerobic Oxidation of Sulfides with a BaRuO₃ Nanoperovskite

Selective Photooxidation of Sulfides Catalyzed by Bis‐cyclometalated Ir^III Photosensitizers Bearing 2,2′‐Dipyridylamine‐Based Ligands

Magnetic Nano-Fe₃O₄-Supported 1-Benzyl-1,4-dihydronicotinamide (BNAH): Synthesis and Application in the Catalytic Reduction of α,β-Epoxy Ketones