18713-58-1Relevant articles and documents
PINACOL REARRANGEMENT OF PHENAGLYCODOL. I. CHARACTERIZATION OF PRODUCTS
MURPHY
, p. 298 - 301 (1964)
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Kamiya,Sugimoto
, p. 2442 (1977)
Competitive Desulfonylative Reduction and Oxidation of α-Sulfonylketones Promoted by Photoinduced Electron Transfer with 2-Hydroxyaryl-1,3-dimethylbenzimidazolines under Air
Hasegawa, Eietsu,Nakamura, Shyota,Oomori, Kazuki,Tanaka, Tsukasa,Iwamoto, Hajime,Wakamatsu, Kan
, p. 2556 - 2569 (2021/02/27)
Desulfonylation reactions of α-sulfonylketones promoted by photoinduced electron transfer with 2-hydroxyarylbenzimidazolines (BIH-ArOH) were investigated. Under aerobic conditions, photoexcited 2-hydroxynaphthylbenzimidazoline (BIH-NapOH) promotes competitive reduction (forming alkylketones) and oxidation (producing α-hydroxyketones) of sulfonylketones through pathways involving the intermediacy of α-ketoalkyl radicals. The results of an examination of the effects of solvents, radical trapping reagents, substituents of sulfonylketones, and a variety of hydroxyaryl- and aryl-benzimidazolines (BIH-ArOH and BIH-Ar) suggest that the oxidation products are produced by dissociation of α-ketoalkyl radicals from the initially formed solvent-caged radical ion pairs followed by reaction with molecular oxygen. In addition, the observations indicate that the reduction products are generated by proton or hydrogen atom transfer in solvent-caged radical ion pairs derived from benzimidazolines and sulfonylketones. The results also suggest that arylsulfinate anions arising by carbon-sulfur bond cleavage of sulfonylketone radical anions act as reductants in the oxidation pathway to convert initially formed α-hydroperoxyketones to α-hydroxyketones. Finally, density functional theory calculations were performed to explore the structures and properties of radical ions of sulfonylketones as well as BIH-NapOH.
Method for preparing aryl ketone based on iron-catalyzed free radical-free radical coupling reaction such as ketonic acid decarboxylation and fatty aldehyde de-carbonylation
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Paragraph 0061-0062, (2020/05/05)
The invention discloses a method for preparing an aryl ketone derivative based on a free radical-free radical cross-coupling reaction such as ketonic acid decarboxylation and fatty aldehyde de-carbonylation. The method comprises the following steps: reacting aryl-substituted ketonic acid with fatty aldehyde under the catalytic action of ferric triacetylacetonate to generate an aryl ketone derivative; the gram-grade reaction can be realized by the method only by using 3mol% of an iron catalyst; and the method has the advantages of no need of consumption of a large amount of a Lewis acid catalyst or a stoichiometric organic metal reagent, mild reaction conditions, one-step reaction, few by-products, wide substrate application range and scalable reaction, and overcomes the defects of large catalyst consumption, insufficient functional group tolerance, many by-products and the like in the prior art.