Further functional group oxidations using sodium perborate

McKillop, Alexander; Kemp, D.M.

doi:10.1016/s0040-4020(01)81008-5

Cited by 199 publications

(136 citation statements)

References 5 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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“…When NaIO 3 was used as the oxidant, the following RC 6 H 4 ICl 2 were obtained: R = H (87%), 4-Br (63%), 3-COOH (80%), 3-COOMe (64%). Of course, only those isomeric RC 6 (i) iodosylarenes dissolved in glacial acetic acid; (ii) (dichloroiodo)arenes in which the chlorine atoms are exchanged by acetoxy groups coming either from silver, lead(II) or sodium acetate, or from acetic acid in the presence of mercury(II) oxide in chlorinated solvents [61]; (iii) iodoarenes are oxidized in warm glacial acetic acid by either peracetic acid, or sodium perborate [51], or electrolytically.…”

Section: A One-pot Methods For Preparing (Dichloroiodo)arenes From Arementioning

confidence: 99%

“…Moreover, pure 2 was synthesized by us in 79% yield with a novel procedure developed in our laboratory [10] (see Section 4.1); this procedure is ca. 5 times cheaper and 8-16 times faster than the former method [51]. Hence, in our work [15] we considerably improved the reported reaction conditions for the iodination of several activated arenes: benzene, iodobenzene, three xylenes, mesitylene, durene, di-and triphenylmethane, fluorene, fluoren-9-one, dibenzofuran, xanth-9-one, and uracil  using just the reagent 2, which is more stable, preparatively more accessible, and notably cheaper than the moisturesensitive reagent 5, strongly recommended by other authors [19b] in place of 2.…”

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confidence: 98%

Organic Iodine(I, III, and V) Chemistry: 10 Years of Development at the Medical University of Warsaw, Poland

Skulski

2000

Molecules

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This review reports some novel (or considerably improved) methods for the synthesis of aromatic iodides, (dichloroiodo)arenes, (diacetoxyiodo)arenes, iodylarenes and diaryliodonium salts, as well as some facile, oxidative anion metatheses in crude diaryliodonium halides and, for comparison, potassium halides. All these new results were obtained in our laboratory over the past decade (1990-2000). A full list of our papers dealing with the organic iodine(I, III and V) chemistry, covering exlusively the aromatic derivatives, is also provided.

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“…The molecular formula of the sodium perborate tetrahydrate anion has two peroxide bridges such as [(HO) 2 BOO] 2 2- (Köroğlu and et al 2003). Sodium perborates are an inexpensive, reliable, and easily stored oxidant (Mckillop and et al 1988). In comparison to hydrogen peroxide, the efficiency of the sodium perborate tetrahydrates can be increased at low temperatures by using TEAD type activators (Bayça et al 2004).…”

Section: Introductionmentioning

confidence: 99%

Bleaching of Bamboo (Phyllostachys bambusoides) Kraft-AQ Pulp with Sodium Perborate Tetrahydrate (SPBTH) after Oxygen Delignification

Okan¹,

Deniz²,

Yildirim³

2013

BioResources

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The most prominent environmental problems facing the paper industry are those due to bleaching processes that use chlorine compounds. In this study, totally chlorine free (TCF) bleaching sequences were applied to Phyllostachys bambusoides bamboo unbleached kraft anthraquinone (AQ) pulp, using different conditions with Oxygen (O) delignification and Sodium Perborate Tetrahydrate (SPBTH) stages. The effects of oxygen pressure, SPBTH ratio, and bleaching time were studied to maximize the brightness gain at the lowest viscosity loss. Unbleached kraft-AQ bamboo pulp was applied to first stage oxygen delignification for bleaching with under 5 bar, 3% NaOH, and 12% concentration conditions. Following the chelated bleaching, Sodium Perborate Tetrahydrate (SPBTH) bleaching was carried out as the final stage. The optimum bamboo kraft pulp bleaching conditions were SPBTH level: 4%, MgSO 4 : 0.5%, Na 2 SiO 3 : 3%, bleaching time: 80 min., reaction temperature: 70°C, and concentration: 12%. An overall increase in the physical properties of paper was evident up to an SPBTH level of 4%. When the SPBTH level and bleaching time increased, the kappa number, viscosity, opacity, and yellowness were decreased, but the brightness was increased. Oxygen delignification with chelatation and SPBTH as a bleaching sequence was shown to be a promising alternative to produce high-quality pulp from bamboo for cleaner paper.

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Further functional group oxidations using sodium perborate

Cited by 199 publications

References 5 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

Organic Iodine(I, III, and V) Chemistry: 10 Years of Development at the Medical University of Warsaw, Poland

Bleaching of Bamboo (Phyllostachys bambusoides) Kraft-AQ Pulp with Sodium Perborate Tetrahydrate (SPBTH) after Oxygen Delignification

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