6956-56-5Relevant academic research and scientific papers
The Synthesis of α-Keto Acetals from Terminal Alkynes and Alcohols via Synergistic Interaction of Organoselenium Catalysis and Electrochemical Oxidation
Ding, Ding,Xu, Liang,Wei, Yu
, p. 4912 - 4917 (2022/03/02)
Herein, an unprecedented electrochemical approach for the synthesis of α-keto acetals has been established from readily available terminal alkynes and alcohols. By merging the electrochemical and organoselenium-catalyzed processes, the desired products are obtained at room temperature in the absence of basic or metallic additives, with carbonyl and acetal motifs incorporated simultaneously across the triple bonds in a single operation.
Rapid, One-Step Synthesis of α-Ketoacetals via Electrophilic Etherification
Paris, Timothy J.,Schwartz, Chris,Sundall, Eric,Willand-Charnley, Rachel
, p. 14797 - 14811 (2021/10/20)
Herein, we report a rapid, one-step synthesis of α-ketoacetals via electrophilic etherification of α-alkoxy enolates and monoperoxyacetals. Methyl, primary, and secondary α-ketoacetals were obtained in 44-63% yields from tetrahydropyranyl substrates; usin
Switchable Synthesis of Sulfoxides and α-Alkoxy-β-ketothioethers Regulated by Temperature in a Selectfluor-Methanol System
Wang, Jiateng,Liu, Mengxia,Zhang, Yue,Bi, Gehua,Zhao, Yi,Yang, Kai,Huang, Xin
, p. 14404 - 14419 (2021/11/01)
A switchable and benign protocol for chemoselective synthesis of sulfoxides and α-alkoxy-β-ketothioethers has been developed. It was determined that various thiophenols and alkenes/alkynes are compatible to realize the target compounds from a medium to a high yield by regulating the reaction temperature. In particular, methanol not only served as a solvent but also participated in the reaction process as a hydrogen donor. In this study, Selectfluor has been proved to be an efficient multifunctional reagent in the reaction system.
Green synthesis of 2, 2-dialkoxy acetophenone derivative
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Paragraph 0017, (2020/04/17)
The invention provides green synthesis of a 2, 2-dialkoxy acetophenone derivative (1), and the structure of the 2, 2-dialkoxy acetophenone derivative (1) is shown as follows, wherein R is alkyl, and R1 is one or more of alkyl, halogen, alkoxy, N, N-dialkylamine or benzoring. According to the method, the 2, 2-dichloroacetophenone derivative, alcohol and alkali are taken as raw materials and are subject to heating and stirring to obtain a target product 2, filtering is performed after the reaction is completed, filtrate is concentrated, and a high-yield and high-purity product can be obtained. The method has the advantages of simple operation, few byproducts, and no generation of any toxic or environmentally harmful substances in the reaction. A new synthesis method is provided for the target product 1.
Synergistic Catalysis of Se and Cu for the Activation of α-H of Methyl Ketones with Molecular Oxygen/Alcohol to Produce α-Keto Acetals?
Chen, Chao,Cao, Zhicheng,Zhang, Xu,Li, Yiming,Yu, Lei,Jiang, Xuefeng
, p. 1045 - 1051 (2020/06/30)
Selenium and copper synergistically catalyzed the oxidation/alkoxylation of methyl ketones to synthesize α-keto acetals directly. Using O2 as oxidant and alcohol as solvent and alkoxylation reagent, the reaction is practical from industrial viewpoint. Mechanistic studies revealed that copper promoted the oxidation of organoselenium intermediates with O2 to allow the key rearrangement and selenoxide syn-elimination regenerating the catalytically active organoselenium species.
Iridium-Catalyzed Asymmetric Hydrogenation of Unsaturated Piperazin-2-ones
Wang, Yanzhao,Liu, Yuanyuan,Li, Kun,Yang, Guoqiang,Zhang, Wanbin
supporting information, p. 1933 - 1941 (2017/06/09)
Two different iridium catalyst systems, generated from the ruthenocene-based phosphine-oxazoline ligand tBu-mono-RuPHOX or the diphosphine ligand BINAP, were developed for the asymmetric hydrogenation of 5,6-dihydropyrazin-2(1H)-ones, affording chiral piperazin-2-ones in good yields and with moderate to good ees. Different catalytic behaviors for the hydrogenation of these types of substrate were observed with these two catalyst systems. Our tBu-mono-RuPHOX ligand, which bears a ruthenocene scaffold with planar chirality, was found to be the best ligand for the [Ir(L)(COD)]BArF catalyst system, affording the desired products with up to 94% ee. (Figure presented.).
Cu-catalyzed aerobic oxygenation of 2-phenoxyacetophenones to alkyloxy acetophenones
Liu, Xinwei,Xu, Huanjun,Ma, Zhishuang,Zhang, Hongye,Wu, Cailing,Liu, Zhimin
, p. 27126 - 27129 (2016/03/25)
Cu-catalyzed aerobic oxygenation of 2-phenoxyacetophenones in the presence of alcohols was reported, and the corresponding alkyl benzoates, alkyloxy acetophenones and phenols were produced in high yields.
New synthesis technology of methyl benzoylformate
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Paragraph 0026, (2017/08/25)
The invention relates to a brand new synthesis technology of a photoinitiator and herbicide metamitron intermediate methyl benzoylformate. The technology has not been reported in literatures. The technology comprises the following steps: acetophenone used as an initial raw material reacts with methyl nitrite under the action of hydrogen chloride to obtain 2,2-dimethoxyacetophenone, 2,2-dimethoxyacetophenone undergoes chlorine chlorination (or bromine bromination) under the catalysis action of a catalyst 4-methyl-2,6-di-tert-butyl phenol, and a molecule of haloalkane is removed from the chlorinated or brominated 2,2-dimethoxyacetophenone to obtain methyl benzoylformate. Influences of hydrogen chloride on the production of 2,2-dimethoxyacetophenone in the reaction and influences of the catalyst 4-methyl-2,6-di-tert-butyl phenol on the production of methyl benzoylformate are researched to determine the optimal conditions of the production of methyl benzoylformate. The new technology provided by the invention is simple to operate, and is economical.
Sodium iodide-catalyzed direct α-alkoxylation of ketones with alcohols via oxidation of α-iodo ketone intermediates
Zhu, Cuiju,Zhang, Yuanfei,Zhao, Huaiqing,Huang, Shijun,Zhang, Min,Su, Weiping
supporting information, p. 331 - 338 (2015/02/19)
The direct α-alkoxylation of ketones with alcohols via a sodium iodide-catalyzed oxidative cross-coupling has been developed. This protocol enables a range of alkyl aryl ketones to cross couple with an array of alcohols in synthetically useful yields. The mechanistic studies provided solid evidence supporting that an α-iodo ketone was a key reaction intermediate, being converted into an α-alkoxylated ketone via further oxidation to a hypervalent iodine species rather than a common nucleophilic substitution, and was generated from the ketone starting material via a radical intermediate. These new mechanism insights should have an effect on the design of iodide-catalyzed oxidative cross-coupling reactions between nucleophiles.
Unusual tandem oxidative C-C bond cleavage and acetalization of chalcone epoxides in the presence of iodine in methanol
Jadhav, Balaso G.,Samant, Shriniwas D.
supporting information, p. 1591 - 1595 (2014/07/08)
An unusual reaction of chalcone epoxides is observed where chalcone epoxides on heating with iodine in methanol leads to α,α- dimethoxyacetophenones, through C-C bond cleavage followed by acetalization of the formyl group. The process occurs through ring
