Tandem Oxidation Processes Using Manganese Dioxide:  Discovery, Applications, and Current Studies

Taylor, Richard J.K.; Reid, Mark; Foot, Jonathan S.; Raw, Steven A.

doi:10.1021/ar050113t

Cited by 304 publications

(124 citation statements)

References 65 publications

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“…Under the proper conditions, 68,375 the reduced oxidant can be removed by a simple filtration to yield an almost pure product. In both reactions, the product solution can often be carried directly to the next step of a reaction sequence.…”

Section: Manganese Dioxide Oxidationsmentioning

confidence: 99%

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Oxoammonium‐ and Nitroxide‐Catalyzed Oxidations of Alcohols

2009

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The discovery in 1959 of stable nitroxide‐based free radicals such as the prototypical 2,2,6,6‐tetramethylpiperidine‐1‐oxyl (TEMPO) led to their use as electron spin resonance (ESR) spin labels in chemistry, biomedicine, and materials science. These nitroxides are prepared by the oxidation of secondary amines that contain no hydrogen atoms on the alpha‐carbons. The unique redox properties of nitroxides enable their use as oxidants in organic synthesis. The varied preparation and uses of oxoammonium salts as stoichiometric oxidants for alcohols are one subject of this review. Oxoammonium ions as oxidants for alcohols have a number of advantages, for example, the method is heavy‐metal free and some of the reactions can be performed in water or aqueous mixtures. A few side reactions are associated with these oxidations. The most serious is the fast reaction of the oxoammonium ion with free amines The several ways these oxidation reactions can be carried out are discussed in detail. They are: Oxidations using stoichimetric quantities of preformed oxoammonium salts carried out in either acidic, neutral, or basic conditions; reactions in which stoichiometric quantities of oxoammonium salts are generated in situ by disproportionation of a nitroxide in the presence of a strong acid; nitroxide‐catalyzed oxidations using a secondary oxidant; efficient nitroxide‐catalyzed oxidations of primary alcohols to carboxylic acids; and oxidations of primary alcohols or hemiacetals that can lead to lactones.

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Section: Manganese Dioxide Oxidationsmentioning

confidence: 99%

“…Manganese dioxide oxidations have been extensively reviewed 376,377 and are the basis of the elegant "tandem oxidation processes". 375 These are reactions in which the manganese oxidation is carried out in a reaction mixture containing a reagent which will further react with the oxidized alcohol.…”

Section: Manganese Dioxide Oxidationsmentioning

confidence: 99%

Oxoammonium‐ and Nitroxide‐Catalyzed Oxidations of Alcohols

2009

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“…In fact, catalytic oxidation reactions play an important role in green organic transformations. From both environmetally and industrially point of views, there is an important demand for greener and more atom efficient approaches that employs aerobic catalytic oxidation processes with minimum amount of waste (Burke and Danheiser 1999;Taylor et al 2005). Thus, the development of new catalytic materials based on biomimetic and green principles such as metallophthalocyanines is of significant importance in organic chemistry (Cornils and Herrmann 1996).…”

Section: Introductionmentioning

confidence: 99%

Copper(II) and iron(II) tetraamino- and tetrasulfophthalocyanines supported on cellulose: synthesis, characterization and catalytic activity on aerobic oxidation of alkyl arenes and alcohols

Shaabani

Hezarkhani

2015

Cellulose

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Functionalized cellulose with copper(II) and iron(II) tetraamino-and tetrasulfophthalocyanines (CuTAPc@cellulose, CuTSPc@cellulose, FeTAPc@ cellulose, and FeTSPc@cellulose) have been synthesized and their structures characterized by FT-IR, elemental analysis, UV-Vis, X-ray diffraction, flame atomic absorption spectroscopy, thermogravimetric analysis, and scanning electron microscopy. The catalytic activity of synthesized catalysts was examined for the aerobic oxidation of alkyl arenes and alcohols to their corresponding carbonyl compounds. We found the best catalyst is the CuTSPc@cellulose from the solvent, conversion, temperature, and reaction time point of views. These catalysts can be readily recycled and reused for several runs without any significant loss of efficiency.

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“…of NaCN to the reaction mixture increased the yields of the required products to 41-77%. Methods were developed for the analogous oxidative transformation of alcohols HetCH 2 OH into the corresponding imines (in the presence of primary amines) [23], oximes [24], and nitriles (in the presence of NH 3 ) [25,26] and also alkenes (in the presence of Ph 3 P + CHBr 2 Br − ) [27][28][29].…”

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confidence: 99%