Manganese‐Promoted Oxidative Cyclization of Unsaturated Oximes Using Molecular Oxygen in Air under Ambient Conditions

Yamamoto, Daisuke; Oguro, Takuto; Tashiro, Yuuki; Soga, Masayuki; Miyashita, K.; Aso, Yukio; Makino, Kazuishi

doi:10.1002/ejoc.201600998

Cited by 28 publications

(13 citation statements)

References 49 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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“…Another approach to the synthesis of hydroxy-substituted isoxazolines 113 is the manganese(III) acetylacetonate catalyzed reaction of β,γ-unsaturated oximes 112 with oxygen of air (Scheme 36) [126].…”

Section: Oxidative Cyclization With the Cleavage Of π-Bond C=cmentioning

confidence: 99%

Oxime radicals: generation, properties and application in organic synthesis

Krylov¹,

Paveliev²,

Budnikov³

et al. 2020

Beilstein J. Org. Chem.

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N-Oxyl radicals (compounds with an N–O• fragment) represent one of the richest families of stable and persistent organic radicals with applications ranging from catalysis of selective oxidation processes and mechanistic studies to production of polymers, energy storage, magnetic materials design and spectroscopic studies of biological objects. Compared to other N-oxyl radicals, oxime radicals (or iminoxyl radicals) have been underestimated for a long time as useful intermediates for organic synthesis, despite the fact that their precursors, oximes, are extremely widespread and easily available organic compounds. Furthermore, oxime radicals are structurally exceptional. In these radicals, the N–O• fragment is connected to an organic moiety by a double bond, whereas all other classes of N-oxyl radicals contain an R2N–O• fragment with two single C–N bonds. Although oxime radicals have been known since 1964, their broad synthetic potential was not recognized until the last decade, when numerous selective reactions of oxidative cyclization, functionalization, and coupling mediated by iminoxyl radicals were discovered. This review is focused on the synthetic methods based on iminoxyl radicals developed in the last ten years and also contains some selected data on previous works regarding generation, structure, stability, and spectral properties of these N-oxyl radicals. The reactions of oxime radicals are classified into intermolecular (oxidation by oxime radicals, oxidative C–O coupling) and intramolecular. The majority of works are devoted to intramolecular reactions of oxime radicals. These reactions are classified into cyclizations involving C–H bond cleavage and cyclizations involving a double C=C bond cleavage.

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“…Recently, Makino et al. reported a manganese‐catalyzed intramolecular oxime‐radical‐mediated dioxygenation of alkenes using molecular oxygen (Scheme ) . Notably, this reaction requires very low loading of Mn(acac) 3 (acac=acetoacetonate) and all manipulations were conducted in air without heating, cooling or use of high pressures.…”

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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Manganese‐Promoted Oxidative Cyclization of Unsaturated Oximes Using Molecular Oxygen in Air under Ambient Conditions

Cited by 28 publications

References 49 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

Oxime radicals: generation, properties and application in organic synthesis

Vicinal anti‐Dioxygenation of Alkenes

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