Microwave-assisted selenium dioxide oxidation of aryl methyl ketones to aryl glyoxals

Young, Ryan M.; Davies‐Coleman, Michael T.

doi:10.1016/j.tetlet.2011.05.130

Cited by 17 publications

(7 citation statements)

References 8 publications

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“…To the best of our knowledge, the pure phenylglyoxal is unstable in air and readily forms the monohydrate and polymers 2b. 14 For further characterization, the more stable crystalline phenylglyoxal monohydrate could be obtained by crystallization from hot water in moderate yield but attempts to isolate crystalline hydrate products from 4‐ tert ‐butylphenylglyoxal and 3,5‐dimethoxyphenylglyoxal failed.…”

Section: Methodsmentioning

confidence: 99%

Gold‐Catalyzed Synthesis of Glyoxals by Oxidation of Terminal Alkynes: One‐Pot Synthesis of Quinoxalines

Shi

Wang

Yang

et al. 2013

Chemistry A European J

136

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Section: Methodsmentioning

confidence: 99%

Gold‐Catalyzed Synthesis of Glyoxals by Oxidation of Terminal Alkynes: One‐Pot Synthesis of Quinoxalines

Shi

Wang

Yang

et al. 2013

Chemistry A European J

136

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“…An improved procedure for the microwave-assisted selenium(IV) oxide oxidation of aryl methyl ketones to aryl glyoxals and diarylethanones to 1,2-etanediones, was elaborated using dimethylsulfoxide as solvent [77,78]. Under focused monomode microwave irradiation, camphor ( 26 ) and camphor sulfonic acid ( 27 ) (Scheme 10), and also camphor sulfonylimine, were oxidized with SeO 2 to the respective 3-oxocompounds 28 and 29 , with the further advantage of an almost quantitative precipitation of elemental selenium which was easy to remove from the reaction mixture by filtration [79].…”

Section: Selenium(iv) Oxide and Selenic(iv) Acid As Oxidizing Agenmentioning

confidence: 99%

Developments in Synthetic Application of Selenium(IV) Oxide and Organoselenium Compounds as Oxygen Donors and Oxygen-Transfer Agents

2015

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A variety of selenium compounds were proven to be useful reagents and catalysts for organic synthesis over the past several decades. The most interesting aspect, which emerged in recent years, concerns application of hydroperoxide/selenium(IV) oxide and hydroperoxide/organoselenium catalyst systems, as "green reagents" for the oxidation of different organic functional groups. The topic of oxidations catalyzed by organoselenium derivatives has rapidly expanded in the last fifteen years This paper is devoted to the synthetic applications of the oxidation reactions mediated by selenium compounds such as selenium(IV) oxide, areneseleninic acids, their anhydrides, selenides, diselenides, benzisoselenazol-3(2H)-ones and other less often used other organoselenium compounds. All these compounds have been successfully applied for various oxidations useful in practical organic syntheses such as epoxidation, 1,2-dihydroxylation, and α-oxyfunctionalization of alkenes, as well as for ring contraction of cycloalkanones, conversion of halomethyl, hydroxymethyl or active methylene groups into formyl groups, oxidation of carbonyl compounds into carboxylic acids and/or lactones, sulfides into sulfoxides, and secondary amines into nitrones and regeneration of parent carbonyl compounds from their azomethine derivatives. Other reactions such as dehydrogenation and aromatization, active carbon-carbon bond cleavage, oxidative amidation, bromolactonization and oxidation of bromide for subsequent reactions with alkenes are also successfully mediated by selenium (IV) oxide or organoselenium compounds. The oxidation mechanisms of ionic or free radical character depending on the substrate and oxidant are discussed. Coverage of the literature up to early OPEN ACCESSMolecules 2015, 20 10206 2015 is provided. Links have been made to reviews that summarize earlier literature and to the methods of preparation of organoselenium reagents and catalysts.

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“…The chiral auxiliary would be removed from the final product, unmasking the chiral amino alcohol scaffold (Scheme B). Arylglyoxals are convenient reagents to prepare nitrogen-containing heterocycles, and well-established methods are known to access substrates with a broad range of modifications, − including oxidation of aryl methyl ketones. − This novel method complements recent developments in the synthesis of morpholines using bifunctional reagents and aldehydes. − …”

Section: Introductionmentioning

confidence: 99%

Asymmetric Synthesis of Chiral 1,2-Amino Alcohols and Morpholin-2-ones from Arylglyoxals

Powell

Walczak

2018

J. Org. Chem.

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Chiral 1,2-amino alcohols are privileged scaffolds with important applications as drug candidates and chiral ligands. Although various methods for the preparation of this structural motif have been reported, these methods are limited because of the use of precious metals and ligands. Here, we report a practical and high yielding synthesis of chiral 1,2-amino alcohols using arylglyoxals and pseudoephedrine auxiliary. This reaction is catalyzed by a Brønsted acid and provides morpholinone products in high yields and selectivities. The morpholine ring was converted into 1,2-amino alcohols in a two-step protocol.

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Microwave-assisted selenium dioxide oxidation of aryl methyl ketones to aryl glyoxals

Cited by 17 publications

References 8 publications

Gold‐Catalyzed Synthesis of Glyoxals by Oxidation of Terminal Alkynes: One‐Pot Synthesis of Quinoxalines

Gold‐Catalyzed Synthesis of Glyoxals by Oxidation of Terminal Alkynes: One‐Pot Synthesis of Quinoxalines

Developments in Synthetic Application of Selenium(IV) Oxide and Organoselenium Compounds as Oxygen Donors and Oxygen-Transfer Agents

Asymmetric Synthesis of Chiral 1,2-Amino Alcohols and Morpholin-2-ones from Arylglyoxals

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