Manganese-catalysed hydroperoxidation of carbon–carbon double bonds using molecular oxygen present in air and hydroxylamine under ambient conditions

Yamamoto, Daisuke; Soga, Masayuki; Ansai, Hiromasa; Makino, Kazuishi

doi:10.1039/c6qo00318d

Cited by 37 publications

(13 citation statements)

References 39 publications

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“…This work is focused on application of manganese(III) acetylacetonate (Mn, Scheme 1, Formula a). Such compound is known as initiator of radical polymerizations [15][16][17][18], mediator in organic synthesis [19,20] and catalyst of oxidation reactions [21,22]. Patent literature reports application of acetylacetone solution of Mn in alkyd-based paints, where it performs as the primary drier [23].…”

Section: Introductionmentioning

confidence: 99%

Performance of Manganese(III) Acetylacetonate in Solvent-Borne and High-Solid Alkyd Formulations

Matušková

Honzı́ček

2020

Materials

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This paper reports a strong drying activity of manganese(III) acetylacetonate. It is documented on several solvent-borne and high-solid alkyd binders. Solubility problems, which often appear upon application of new primary driers, were overcome by use of dimethyl sulfoxide. Interestingly, intense coloration of the drier does not influence the transparent paint films due to in situ reduction to manganese(II) as evidenced by colorimetric measurements. Kinetics of the autoxidation process was investigated by infrared and Raman spectroscopy. For selected formulation, the effect of film thickness on through drying was estimated by infrared spectroscopy using attenuated total reflection sampling technique.

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Section: Introductionmentioning

confidence: 99%

Performance of Manganese(III) Acetylacetonate in Solvent-Borne and High-Solid Alkyd Formulations

Matušková

Honzı́ček

2020

Materials

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“…reported a manganese‐catalyzed efficient hydroperoxidation of styrene derivatives using NHPI, NHS or N ‐hydroxybenzotriazole (HOBt) as radical surrogates with the flask open to the air. The dioxygenated products 64 were afforded with moderate anti selectivities (Scheme ) …”

Section: Anti‐dioxygenation By Radical Pathwaysmentioning

confidence: 99%

Vicinal anti‐Dioxygenation of Alkenes

Wang

2018

Asian J Org Chem

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Vicinal diols and their derivatives are common motifs in al arge number of biologically active compounds and are also important intermediates in organics ynthesis. To achieve these structural units in ah ighly stereoselective manner,d irect dioxygenation of simple alkene precursors has provedt ob et he most straightforward approach, and thus many practical proceduresu sing various strategies have been developed. In this Focus Review ac oncise summary of the main methods for anti-dioxygenation of olefins is presented. Scheme1.Categories of vicinal anti-dioxygenation of alkenes.[a] Prof.Scheme6.Ammonium-directed formal anti-dioxygenation as key step for the synthesis of aza-and amino sugars.Scheme7.N-Oxide-directed formal anti-dihydroxylation.Scheme8.NafionN R50-catalyzed anti-dihydroxylation.Scheme9.PTSA-catalyzed anti-dihydroxylation.Scheme14. SeO 2 -catalyzed anti-dihydroxylation.Scheme15. Diselenide-catalyzed anti-dihydroxylationo fcyclohexene.Scheme16. Chiral-diselenide-catalyzed asymmetric anti-dihydroxylation.

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“…[22] Thus, iron(III)-catalyzed oxidation of the N-hydroxylamines with air can produce N-oxyl radicals a, which on addition with olefin can give the C-centered radicals b. [24] Styrenes with different substituents underwent reaction to produce hydroperoxides in excellent yields. The Fe III -oxo species d may undergo homolysis to yield N-oxyl radicals and Fe II that can be oxidized to Fe III under air.…”

Section: Intermolecular Dioxygenationsmentioning

confidence: 99%

Recent Advances in Radical Dioxygenation of Olefins

Bag

Pradhan

et al. 2017

Eur J Org Chem

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Dioxygenation of olefins is a valuable synthetic tool for the construction of 1,2‐diols and α‐oxygenated ketones. The use of radical approaches to achieve this direct 1,2‐difunctionalization has recently made considerable progress. The metal‐catalyzed reactions employ molecular oxygen and air as the oxidants, whereas metal‐free dioxygenation utilizes oxygen and peroxides. These oxidations are effective under mild conditions, with activated olefins found to be the most successful substrates. This microreview covers the recent developments in the radical dioxygenation of olefins, with respect to substrate scope, mechanism, and the advantages and disadvantages of the methods.

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Manganese-catalysed hydroperoxidation of carbon–carbon double bonds using molecular oxygen present in air and hydroxylamine under ambient conditions

Abstract: A highly efficient manganese-catalysed hydroperoxidation of carbon–carbon double bonds of enynes as well as styrene derivatives using N-hydroxyphthalimide, N-hydroxybenzotriazole or N-hydroxysuccinimide was developed.

Cited by 37 publications

References 39 publications

Performance of Manganese(III) Acetylacetonate in Solvent-Borne and High-Solid Alkyd Formulations

Performance of Manganese(III) Acetylacetonate in Solvent-Borne and High-Solid Alkyd Formulations

Vicinal anti‐Dioxygenation of Alkenes

Recent Advances in Radical Dioxygenation of Olefins

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