70091-75-7Relevant articles and documents
Electrochemical two-electron oxygen reduction reaction (ORR) induced aerobic oxidation of α-diazoesters
Chen, Liang,Gao, Meng,Lu, Cuifen,Ma, Chao,Ruan, Mengyao,Wen, Ziyang,Yang, Fan,Yang, Guichun
, p. 2168 - 2171 (2022/02/17)
Electrochemical oxygen reduction reaction (ORR) is a powerful tool for introducing oxygen functional groups in synthetic chemistry. However, compared with the well-developed one-electron oxygen reduction process, the applications of two-electron oxygen re
Tris(pentafluorophenyl)borane-Catalyzed Oxygen Insertion Reaction of α-Diazoesters (α-Diazoamides) with Dimethyl Sulfoxide
Gao, Wen-Xia,Liu, Miao-Chang,Wu, Hua-Yue,Wu, Xiao-Yang,Zhou, Yun-Bing
supporting information, (2022/01/19)
A tris(pentafluorophenyl)borane-catalyzed oxidation reaction of α-diazoesters (α-diazo amides) with dimethyl sulfoxide has been developed. The reaction proceeds under metal free conditions to afford a series α-ketoesters and α-ketoamides. The synthetic utility of this protocol is demonstrated through synthetic transformations and scaled-up synthesis. (Figure presented.).
Green preparation method of aryl [alpha]-keto ester compound
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Paragraph 0081-0084, (2020/05/30)
The invention discloses a green preparation method of an aryl [alpha]-keto ester compound. The method comprises the specific steps that an [alpha]-diazo compound serves as a reaction raw material, copper sulfate serves as a catalyst, water serves as a solvent, a target product aryl [alpha]-keto ester compound is prepared through a reaction at the temperature of 60 DEG C, the structural general formula of the [alpha]-diazo compound is shown in the specification, and the structural general formula of the correspondingly prepared target product aryl [alpha]-keto ester compound is shown in the specification. The method for synthesizing the target product aryl [alpha]-keto ester compound by catalyzing the [alpha]-diazo compound derivative with copper sulfate has the advantages that the reactioncondition is green and mild, the catalyst is cheap and easy to obtain, the operation is simple and convenient, the yield is relatively high, the universality of a reaction substrate is wide, and thelike.
Controllable chemoselectivity in the coupling of bromoalkynes with alcohols under visible-light irradiation without additives: Synthesis of propargyl alcohols and α-ketoesters
Ni, Ke,Meng, Ling-Guo,Ruan, Hongjie,Wang, Lei
supporting information, p. 8438 - 8441 (2019/07/22)
The chemoselectivity of visible-light-induced coupling reactions of bromoalkynes with alcohols can be controlled by simple changes to the reaction atmosphere (N2 or O2). A N2 atmosphere favours propargyl alcohols via a direct C-C coupling process, whereas an O2 atmosphere results in the generation of α-ketoesters through the oxidative CC/C-O coupling pathway.
Lewis acid catalyzed cascade annulation of alkynols with α-ketoesters: A facile access to γ-spiroketal-γ-lactones
Kambale, Digambar A.,Thorat, Sagar S.,Pratapure, Madhukar S.,Gonnade, Rajesh G.,Kontham, Ravindar
supporting information, p. 6641 - 6644 (2017/07/10)
A novel Lewis acid catalyzed intermolecular cascade annulation of alkynols with α-ketoesters has been developed. This simple and efficient cascade annulation proceeds through a 5-exo-dig cyclization of alkynols followed by annulation with α-ketoester to provide a wide variety of unsaturated γ-spiroketal-γ-lactones (1,6-dioxaspiro[4.4]non-3-en-2-ones) related to many natural products.
Copper-catalyzed TEMPO oxidative cleavage of 1,3-diketones and β-keto esters for the synthesis of 1,2-diketones and α-keto esters
Zhou, Peng-Jun,Li, Cheng-Kun,Zhou, Shao-Fang,Shoberu, Adedamola,Zou, Jian-Ping
, p. 2629 - 2637 (2017/04/03)
A copper-catalyzed efficient and practical method has been developed for the synthesis of 1,2-diketones and α-keto esters. TEMPO was used as a radical initiator and scavenger, oxidizing the cleavage of α-methylene of 1,3-diketones and β-keto esters to form 1,2-diketones and α-keto esters. This method provided a general way for the formation of 1,2-dicarbonyl compounds.
Novel Synthesis of α-Keto Esters and Amides by an sp3 C-H Oxidation of Nitromethyl Aryl Ketones Promoted by Ion-Supported (Diacetoxyiodo)benzene
Jiang, Xiaoying,Gan, Bing,Liu, Jiwei,Xie, Yuanyuan
supporting information, p. 2737 - 2741 (2016/11/25)
A simple and efficient method is described for the preparation of α-keto esters or amides from nitromethyl aryl ketones. In the presence of nucleophiles (alcohols or amines), the ion-supported (di-acetoxyiodo)benzene-promoted sp3 C-H oxidation of nitromethyl aryl ketones proceeded efficiently under mild conditions to give the corresponding α-keto esters and amides in moderate to good yields. This is the first reported use of (diacetoxyiodo)benzene in the synthesis of α-keto esters and amides. The reaction is ecofriendly and has the -advantages of mild conditions, short reaction times, and a recyclable reagent.
In Situ Generated AgII-Catalyzed Selective Oxo-Esterification of Alkyne with Alcohol to α-Ketoester: Photophysical Study
Laha, Radha M.,Khamarui, Saikat,Manna, Saikat K.,Maiti, Dilip K.
supporting information, p. 144 - 147 (2016/01/12)
An expert and easy one-step catalytic method for the multi O-C coupling of alkyne is developed for the synthesis of valuable α-ketoesters and their chiral analogues, in contrast to the generation of esters by a noncatalytic method. The in situ generated powerful AgII catalyst from AgOTf is the workhorse in the oxidative grafting of alkyne with PhIO and alcohol. The radical mechanism is confirmed in our controlled experiments and UV-vis study.
Reactions of organolithiums with dialkyl oxalates. A flow microreactor approach to synthesis of functionalized α-keto esters
Nagaki, Aiichiro,Ichinari, Daisuke,Yoshida, Jun-Ichi
supporting information, p. 3242 - 3244 (2013/05/08)
Reactions of functionalized aryllithiums with dialkyl oxalates were achieved using a flow microreactor to obtain α-keto esters with high selectivity by virtue of fast 1:1 micromixing.
BF3 · Et2O-induced decomposition of ethyl 2-diazo-3-hydroxy-3,3-diarylpropanoates in acetonitrile: A novel approach to 2,3-diaryl β-enamino ester derivatives
Gioiello, Antimo,Venturoni, Francesco,Natalini, Benedetto,Pellicciari, Roberto
supporting information; experimental part, p. 3520 - 3523 (2009/09/30)
The BF3·Et2O-induced decomposition of ethyl 2-diazo-3-hydroxy-3,3-diarylpropanoates, prepared by the addition of a series of benzophenones to ethyl diazo(lithio)acetate, is reported and studied. By using acetonitrile as a solvent, the corresponding N-acyl β-enamino ester derivatives are obtained in good yields and with a diverse regioselectivity as the result of 1,2-aryl migration in the vinyl cation intermediates. The factors that govern the migratory aptitude as well as the mechanistic aspects of the reaction are discussed.