Reactions using micellar systems: Biomimetic type oxygenation of indoles catalyzed by cobalt(II)-schiff's base complexes.

Inada, Akira; Nakamura, Y.; Morita, Yutaka

doi:10.1248/cpb.36.462

Cited by 8 publications

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“…Inada et al reported a Co(salen)catalyzed trimerization of indoles with sodium dodecylsulfate as surfactant under O 2 bubbling. [4] Recently, the 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO)-mediated oxidation of indoles with O 2 using benzoic acid as an additive was also reported. [5] In addition, a visible-light photoredox catalysis has been devel-oped for the trimerization of indoles with ruthenium or natural chlorophyll as photocatalyst.…”

Section: Introductionmentioning

confidence: 99%

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Green Oxidation of Indoles Using Molecular Oxygen over a Copper Nitride Nanocube Catalyst

Yamaguchi

Mitsudome

et al. 2022

Eur J Org Chem

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Oxidative transformation of indoles is a promising approach for synthesizing valuable nitrogen-containing compounds; however, conventional methods use toxic oxidants and additives. Herein, we report for the first time the catalytic oxidative trimerization and the oxygenative cleavage (Witkop oxidation) of indoles using molecular oxygen under additive-free conditions accomplished by a copper nitride nanocube (Cu 3 N NC) catalyst. The Cu 3 N NC catalyst exhibits excellent activity to produce various indolin-3-ones and 2-ketoanilides with high functional group tolerance. Owing to this excellent catalytic performance, the Cu 3 N NC catalyst is distinguished from the conventional copper catalysts, demonstrating the high catalytic potential of metal nitride in organic synthesis.

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Section: Introductionmentioning

confidence: 99%

“…Inada et al. reported a Co(salen)‐catalyzed trimerization of indoles with sodium dodecylsulfate as surfactant under O 2 bubbling [4] . Recently, the 2,2,6,6‐tetramethylpiperidine‐1‐oxyl (TEMPO)‐mediated oxidation of indoles with O 2 using benzoic acid as an additive was also reported [5] .…”

Section: Introductionmentioning

confidence: 99%

Green Oxidation of Indoles Using Molecular Oxygen over a Copper Nitride Nanocube Catalyst

Yamaguchi

Mitsudome

et al. 2022

Eur J Org Chem

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“…The unique ability of micelles to solubilize organic substrates in water and to catalyze chemical reactions, forms the basis for their use as a medium for investigating organic and bioorganic processes [1][2][3][4][5][6][7].…”

Section: Introductionmentioning

confidence: 99%

Oxidation of 2,6-Di-tert-butylphenol by dioxygen catalyzed by tetrasodium phthalocyaninatocobalt(II) tetrasulfonate in aqueous micellar media

Hassanein

Sakaran

Shendy

2010

JICS

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The oxidation of 2,6-di-tert-butylphenol by dioxygen has been investigated in aqueous micellar aggregates of cetyltrimethylammonium bromide (CTAB) using tetrasodium phthalocyaninatocobalt(II) tetrasulfonate (CoPcTsNa 4 ) as catalyst. The CTAB/CoPcTsNa 4 system showed enhanced catalytic activity in the oxidation of 2,6-di-tert-butylphenol compared to that observed in the oxidation reaction in the absence of CTAB. 2,6-Di-tert-butyl-1,4-benzoquinone and 3,5,3',5'-tetra-tert-butyl-4,4-diphenoquinone were identified as reaction products. The initial rate constants of auto-oxidation reaction was found to increase with increasing the pH range from 7.0 to 13.0. The rate constants k obs of auto-oxidation reaction showed linear dependence on catalyst concentration. The rate of auto-oxidation reaction was found to fit a Michealis-Menten kinetic model for the saturation of catalyst sites with increasing 2,6-di-tert-butylphenol concentration and dioxygen pressure. Tetrasodium phthalocyaninatocobalt(II) tetrasulfonate in aqueous micellar solution of CTAB was found to be mainly monomeric.

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“…However, an added versatility of these compounds is their ability to oxidize the C2−C3 double bond of indoles . Other reagents which oxidize the indole C2−C3 double bond to various products depending on the indole substitution pattern are dimethyldioxirane, singlet oxygen, m -CPBA or MMPP, Co(salen), thallium(III) acetate, thallium(III) nitrate, N -chlorobenzotriazole, and DDQ . During the course of developing a synthesis of the natural product, mitomycin C (Figure ), we discovered that use of MoO 5 ·HMPA oxidizes the C9−9a double bond of azidomitosene 1 to give a ∼2:1 mixture of the diastereomeric methoxy ketones 7a and 7b in one step .…”

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confidence: 99%

Oxidation of Indole Substrates by Oxodiperoxomolybdenum·Trialkyl(aryl)- phosphine Oxide Complexes

2004

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Reactions using micellar systems: Biomimetic type oxygenation of indoles catalyzed by cobalt(II)-schiff's base complexes.

Cited by 8 publications

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Green Oxidation of Indoles Using Molecular Oxygen over a Copper Nitride Nanocube Catalyst

Green Oxidation of Indoles Using Molecular Oxygen over a Copper Nitride Nanocube Catalyst

Oxidation of 2,6-Di-tert-butylphenol by dioxygen catalyzed by tetrasodium phthalocyaninatocobalt(II) tetrasulfonate in aqueous micellar media

Oxidation of Indole Substrates by Oxodiperoxomolybdenum·Trialkyl(aryl)- phosphine Oxide Complexes

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