Iodoxybenzene

Sharefkin, J. G.; Saltzman, H.

doi:10.1002/0471264180.os043.20

Cited by 18 publications

(27 citation statements)

References 4 publications

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“…We encountered difficulty in this regeneration step. The general methods for preparing PIDA using peracetic acid 24) and other inorganic oxidants, such as sodium perborate 25) and sodium periodate, 26) were first examined for the tetraiodides 1Ј with only low yields of the desired 1a. After further investigations, we found a new synthetic method of trivalent diacetate using meta-chloroperbenzoic acid (mCPBA) and succeeded in synthesizing 1a in nearly quantitative yield using mCPBA in a dilute dichloromethane/acetic acid mixed solvent system under homogeneous conditions at room temperature, by which the key regeneration step affecting the effectiveness of the net recycling process shown in Chart 3 was well established.…”

Section: Development Of New Methods For Recycling and Catalytic Use Omentioning

confidence: 99%

Recycling and Catalytic Approaches for the Development of a Rare-Metal-Free Synthetic Method Using Hypervalent Iodine Reagent

Dohi

2010

CHEMICAL & PHARMACEUTICAL BULLETIN

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Oxidation reactions consist of a number of important transformations in organic synthesis. However, in spite of their utility in both laboratory-and industrial-scale production, oxidations are among the most problematic processes regarding the factors of safety, environmental friendliness, operational simplicity, etc. As oxidants, hypervalent iodines, such as phenyliodine(III) diacetate (PIDA) and phenyliodine(III) bis(trifluoroacetate) (PIFA), are among promising reagents for developing environmentally benign oxidation reactions due to their low toxicities, mild reactivity, ready availability, high stability, and easy handling. Our research objective is, largely in consideration of economic and environmental viewpoints, to enhance the synthetic values of these reagents as useful alternatives to highly toxic heavy-metal oxidants and even rare transition metals by pioneering their efficient utilization methods and unique reactivities. During this study, we have succeeded in the development of new recyclable reagents 1 and their catalytic utilization, and the design of a new chiral reagent 2 and its application to perform asymmetric oxidations. Accordingly, the recycling and catalytic use of a hypervalent iodine reagent became possible in many representative types of oxidative bond-forming reactions, some of which even include key transformations for natural product synthesis. A summary of these important achievements in hypervalent iodine chemistry are described in this review.

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Section: Development Of New Methods For Recycling and Catalytic Use Omentioning

confidence: 99%

Recycling and Catalytic Approaches for the Development of a Rare-Metal-Free Synthetic Method Using Hypervalent Iodine Reagent

Dohi

2010

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…Iodosylbenzene (PhIO) was prepared by hydrolysis of iodosylbenzene diacetate, according to the method of Sharefkin and Saltzmann; 13,14 its purity was 94% as measured by iodometric titration. 15 Hydrogen peroxide was stored at 5 °C and titrated periodically.…”

Section: Methodsmentioning

confidence: 99%

Hydrocarbon oxidation catalyzed by iron and manganese porphyrins anchored on aminofunctionalized supports

Faria¹,

Leod²,

Barros³

et al. 2009

J. Braz. Chem. Soc.

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As metaloporfirinas de segunda geração (MePs), cloreto de [5,10,15,20-tetraquis(pentafluorofenil)porfirinaferro(III)], FeP, e cloreto de [5,10,15,20-tetraquis(pentafluorofenil)porfirinamanganês(III)], MnP, foram covalentemente ancoradas em suportes aminofuncionalizados, com o objetivo de preparar catalisadores sólidos seletivos para a oxidação de compostos orgânicos. Montmorillonita K10 funcionalizada com 3-aminopropiltrietoxissilano (Mont1) ou com 3-cloropropiltrietoxissilano seguida por reação com 1,6-diaminoexano (Mont2), e sílica gel funcionalizada com 3-aminopropiltrietoxissilano (Sil1) ou modificada com 3-cloropropiltrietoxissilano seguida por reação com 1,6-diaminoexano (Sil2) foram preparadas e caracterizadas por UV-Vis, IR, EPR, TGA e difratometria de raios X. As atividades catalíticas das MePs imobilizadas nestes suportes foram investigadas na oxidação de (Z)-cicloocteno, cicloexano e estireno por iodosilbenzeno (PhIO) ou H 2 O 2 . Os sistemas estudados foram catalisadores eficientes da oxidação de todos os substratos, especialmente utilizando PhIO como oxidante. Não se observou lixiviamento das MePs dos suportes, indicando que a ligação covalente é um método muito eficiente para a imobilização de catalisadores. As FePs imobilizadas foram catalisadores mais eficientes que as correspondentes MnPs, mesmo quando imidazol foi empregado como um co-catalisador para as MnPs ancoradas. Embora os rendimentos de produtos oxidados utilizando H 2 O 2 tenham sido mais baixos que aqueles obtidos com PhIO, alguns sistemas heterogêneos envolvendo MePs foram mais eficientes que as correspondentes MePs em solução, tanto em termos de rendimento de produto quanto de seletividade.The second-generation metalloporphyrins (MePs) [5,10,15,20-tetrakis(pentafluorophen yl)porphyrin iron(III)] chloride, FeP, and [5,10,15,20-tetrakis(pentafluorophenyl)porphyrin manganese(III)] chloride, MnP, were covalently attached to aminofunctionalized supports, with a view to preparing selective solid catalysts for the oxidation of organic compounds. Montmorillonite K10 functionalized with 3-aminopropyltriethoxysilane (Mont1) or modified with 3-chloropropyltriethoxysilane followed by reaction with 1,6-diaminohexane (Mont2), and silica gel functionalized with 3-aminopropyltriethoxysilane (Sil1) or modified with 3-chloropropyltriethoxysilane followed by reaction with 1,6-diaminohexane (Sil2) were synthesized and characterized by UV-Vis and IR spectroscopies, EPR, TGA, and X-ray diffractometry. The catalytic activities of the MePs immobilized on these supports were investigated for the oxidation of (Z)-cyclooctene, cyclohexane and styrene by PhIO or H 2 O 2 . The studied systems were efficient catalysts for the oxidation of all substrates, especially when PhIO was the oxidant. There was no MeP leaching from the supports, indicating that covalent binding is a very efficient method for catalyst immobilization. The immobilized FePs were more efficient catalysts than the corresponding MnPs, even when imidazole was employed as a cocatalyst for the supp...

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“…Iodosylbenzene was prepared from iodobenzene in two steps, following the method described by Saltzmann and Sharefkin. 29 Its purity (97%) was determined by iodometric titration. Kiesegel 60 Merck (230-400 mesh) silica gel was used for column chromatography.…”

Section: Methodsmentioning

confidence: 99%

Tetra-crowned porphyrin as P450 biomimetic model for carbamazepine oxidation

Filho¹,

Leod²,

Gotardo³

et al. 2009

Arkivoc

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A substituted porphyrin bearing four crown ether units, H 2 (TCP), was synthesized from the reaction between (5,10,15,20-tetra(o-aminophenyl)porphyrin) and the acyl derivative of the ether (4-carboxy-18-crown-6). The free-base porphyrin was characterized by C, N, and H elemental analysis; UV-vis and IR spectroscopies; and 1 H NMR. The corresponding ironporphyrin, Fe(TCP)Cl, was obtained via iron insertion into H 2 (TCP). Fe(TCP)Cl was employed as catalyst for carbamazepine (CBZ) oxidation by iodosylbenzene (PhIO), 3-chloroperoxybenzoic acid (m-CPBA) or sodium hypochlorite (NaOCl), in methanol or in a biphasic water/dichloroethane system. The crowned ironporphyrin proved to be a highly efficient and selective catalyst for CBZ epoxidation even in the biphasic dichloroethane /H 2 O system, with no need for an additional phase transfer agent.

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Iodoxybenzene

Abstract: Iodoxybenzene product: iodoxybenzene

Cited by 18 publications

References 4 publications

Recycling and Catalytic Approaches for the Development of a Rare-Metal-Free Synthetic Method Using Hypervalent Iodine Reagent

Recycling and Catalytic Approaches for the Development of a Rare-Metal-Free Synthetic Method Using Hypervalent Iodine Reagent

Hydrocarbon oxidation catalyzed by iron and manganese porphyrins anchored on aminofunctionalized supports

Tetra-crowned porphyrin as P450 biomimetic model for carbamazepine oxidation

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