Uses of Sodium Chlorite and Sodium Bromate in Organic Synthesis. A Review

Krapcho, A. Paul

doi:10.1080/00304940609355988

Cited by 20 publications

(12 citation statements)

References 148 publications

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“…Both TES ether functions were cleaved and oxidized under Swern reaction conditions, and the resulting crude keto aldehyde was subjected immediately to further oxidation to the carboxylic acid and subsequent esterification with trimethylsilyldiazomethane. Keto ester 32 was obtained in a good 72% yield from 3 .…”

Section: Resultsmentioning

confidence: 99%

Toward the Elucidation of the Metabolism of 15-E₂-Isoprostane: The Total Synthesis of the Methyl Ester of a Potential Central Metabolite

Jahn

Dinca

2010

J. Org. Chem.

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An 11-step total synthesis of the methyl ester of a potential metabolite of the autoxidatively formed natural product 15-E(2)-IsoP, whose metabolism is not known, is reported. Several vinylogous Mukaiyama aldol additions were tested for the assembly of the acyclic C7-C20 precursor. A new oxidative dianion cyclization served to access the cyclopentane core. The full carbon skeleton was synthesized by an acetylide alkylation. The overall yield of the metabolite amounts to 1.4% for the most efficient route. The results demonstrate convincingly that E(2)-IsoP metabolites are highly epimerization-sensitive and that they may thus also contribute to PGE(2)-action and metabolism.

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Section: Resultsmentioning

confidence: 99%

Toward the Elucidation of the Metabolism of 15-E₂-Isoprostane: The Total Synthesis of the Methyl Ester of a Potential Central Metabolite

Jahn

Dinca

2010

J. Org. Chem.

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“…While sodium chlorite, a cheap inorganic salt, has been mainly used in water treatment and textile industries, 3 in synthetic organic chemistry it has found its primary application in the oxidation of aldehydes to carboxylic acids (Scheme 1a). 4,5 Although there is an increasing number of reports regarding its use in organic synthesis, no doubts that the Pinnick oxidation is by far the most representative example of using this chemical reagent in synthesis. However, further applications in synthesis are the direct oxidation of alcohols to their respective carboxylic acids (Scheme 1b), 6 the one-pot oxidative cleavage of terminal 1,2-diols to dehomologated carboxylic acids (Scheme 1c), 7 the epoxidation of olefins (Scheme 1d), 8 the C-H oxidation of olefines to their corresponding enones (Scheme 1e), 9 and in the se-…”

Section: Introductionmentioning

confidence: 99%

Transition-Metal-Free Functionalization of Saturated and Unsaturated Amines to Bioactive Alkaloids Mediated by Sodium Chlorite

Romero‐Ibañez¹,

Fuentes²,

Sartillo‐Piscil³

2020

Synlett

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New approaches to the synthesis of alkaloids through the straightforward functionalization of C(sp3)–H and C(sp2)=C(sp2) bonds of simple five and six-membered ring N-heterocycles are highlighted. The direct functionalization of preexisting N-heterocycles to advanced alkaloids intermediates is a chemical operation that commonly requires the intervention of transition or precious metals. Regardless the inherent unwanted waste production, the high economical cost of many transition metal catalysts limits their use globally. Here, we account our efforts directed toward the synthesis of bioactive alkaloids under an economic and ecological fashion by using NaClO2 as the key activating or oxidizing reagent that substitutes the use of transition metal catalysts. While undesired metal wastes are collected during the extraction process of a transition metal catalyzed reaction, innocuous NaCl is the commonly product waste when NaClO2 is employed in our chemical transformations. Beginning with the synthesis of 2,3-epoxyamides from allyl amines, we concluded with the functionalization of multiple and remote C(sp3)-H and C(sp3)–C(sp3) bonds in piperidine rings that enabled the preparation of important bioactive alkaloids. For the latter functionalization, a precise amount of co-oxidant reagent (NaOCl) and radical 2,2,6,6-tetramethylpiperidinyloxy (TEMPO) were needed.

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“…Sodium bromate is an inexpensive important oxy-halo oxidant which has proved to be a versatile reagent in effecting a variety of oxidation reactions, 16 and for the oxidative cleavage of alkyl and trimethylsilyl ethers and ethylene acetals to the corresponding carbonyl compounds. 17,18 Imidazolium cation based ionic liquids have received considerable attention in recent years 19 because of their unique physical and chemical properties such as thermal stability, recyclability and ability to dissolve a large range of organic and inorganic compounds.…”

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confidence: 99%

The Highly Selective Metal-Free Oxidation of Sulfides, Tellurides and Phosphines Using Sodium Bromate in the Presence of Recyclable Ionic Liquid [Bmim]HSO₄, at 80 °C

Rajeswari

Lumb

Khurana

2016

Journal of Chemical Research

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The metal-free oxidation of sulfides to sulfones using sodium bromate (NaBrO3) in [bmim]HSO4:H2O (3:1, v/v) at 80 °C is reported. Phenylalkyl, phenylbenzyl, diaryl and heteroaryl sulfides were transformed to the corresponding sulfones. Aryl tellurides and phosphines were oxidised to the corresponding telluroxides and phosphine oxides. All the reactions proceeded smoothly and gave high yields in 20–55 min. The ionic liquid [bmim]HSO4 was easily recovered and recycled.

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Uses of Sodium Chlorite and Sodium Bromate in Organic Synthesis. A Review

Cited by 20 publications

References 148 publications

Toward the Elucidation of the Metabolism of 15-E₂-Isoprostane: The Total Synthesis of the Methyl Ester of a Potential Central Metabolite

Toward the Elucidation of the Metabolism of 15-E₂-Isoprostane: The Total Synthesis of the Methyl Ester of a Potential Central Metabolite

Transition-Metal-Free Functionalization of Saturated and Unsaturated Amines to Bioactive Alkaloids Mediated by Sodium Chlorite

The Highly Selective Metal-Free Oxidation of Sulfides, Tellurides and Phosphines Using Sodium Bromate in the Presence of Recyclable Ionic Liquid [Bmim]HSO₄, at 80 °C

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Uses of Sodium Chlorite and Sodium Bromate in Organic Synthesis. A Review

Cited by 20 publications

References 148 publications

Toward the Elucidation of the Metabolism of 15-E2-Isoprostane: The Total Synthesis of the Methyl Ester of a Potential Central Metabolite

Toward the Elucidation of the Metabolism of 15-E2-Isoprostane: The Total Synthesis of the Methyl Ester of a Potential Central Metabolite

Transition-Metal-Free Functionalization of Saturated and Unsaturated Amines to Bioactive Alkaloids Mediated by Sodium Chlorite

The Highly Selective Metal-Free Oxidation of Sulfides, Tellurides and Phosphines Using Sodium Bromate in the Presence of Recyclable Ionic Liquid [Bmim]HSO4, at 80 °C

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Toward the Elucidation of the Metabolism of 15-E₂-Isoprostane: The Total Synthesis of the Methyl Ester of a Potential Central Metabolite

Toward the Elucidation of the Metabolism of 15-E₂-Isoprostane: The Total Synthesis of the Methyl Ester of a Potential Central Metabolite

The Highly Selective Metal-Free Oxidation of Sulfides, Tellurides and Phosphines Using Sodium Bromate in the Presence of Recyclable Ionic Liquid [Bmim]HSO₄, at 80 °C