62936-34-9Relevant academic research and scientific papers
Photoinduced Diverse Reactivity of Diazo Compounds with Nitrosoarenes
Roy, Sourav,Kumar, Gourav,Chatterjee, Indranil
, p. 6709 - 6713 (2021/09/08)
A diverse reactivity of diazo compounds with nitrosoarene in an oxygen-transfer process and a formal [2 + 2] cycloaddition is reported. Nitosoarene has been exploited as a mild oxygen source to oxidize an in situ generated carbene intermediate under visible-light irradiation. UV-light-mediated in situ generated ketenes react with nitosoarenes to deliver oxazetidine derivatives. These operationally simple processes exemplify a transition-metal-free and catalyst-free protocol to give structurally diverse α-ketoesters or oxazetidines.
Preparation method of alpha-ketoester compound
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Paragraph 0138-0141, (2021/04/21)
The invention discloses a preparation method of an alpha-ketone ester compound. The method specifically comprises the following operation steps: adding raw materials alpha-diazo ester and an organic photocatalyst into a reaction flask, then adding an organic solvent, and reacting for 2-12 hours in air at room temperature under the irradiation of a visible light lamp; after the reaction is monitored by thin-layer chromatography (TLC), stopping the reaction, and extracting a reaction solution by using ethyl acetate; concentrating the extracting solution under reduced pressure to obtain a crude product, and performing column chromatography separation on the crude product to obtain the alpha-diazonium ester compound. According to the preparation method, clean visible light is used as reaction energy, cheap organic dye is used as a photocatalyst, air is used as a green oxidizing agent and an oxygen source, and the preparation method has the advantages of simplicity and convenience in operation, no metal residue and mild reaction conditions.
Copper(I)-catalyzed aerobic oxidation of α-diazoesters
Xu, Changming,Bai, Lei,Wang, Yongchang
, p. 12579 - 12584 (2020/11/09)
A practical Cu-catalyzed oxidation of α-diazoesters to α-ketoesters using molecular oxygen as an oxidant has been developed. Both electron-poor and electron-rich aryl α-diazoesters are suitable substrates and provide the α-ketoesters in good yields. In this oxidative system, α-diazo-β-ketoesters are also compatible as substrates but unexpectedly furnish α-ketoesters via C-C bond cleavage, rather than the vicinal tricarbonyl products.
Green preparation method of aryl [alpha]-keto ester compound
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Paragraph 0045-0048, (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.
Highly adequate oxidative esterification of α-carbonyl aldehydes with alkyl halides in TBAI/TBHP mediated system
Bhargude, Pooja L.,Lade, Jatin J.,Patil, Bhausaheb N.,Vadagaonkar, Kamlesh S.,Chaskar, Atul C.
supporting information, p. 1325 - 1333 (2019/04/30)
An efficient and viable synthesis of α-ketoesters from alkyl halides and α-carbonyl aldehydes has been reported under metal-free conditions. The present method involves oxidative esterification of α-carbonyl aldehydes with alkyl halide using TBAI as a promoter and TBHP as an oxidant to form α-ketoesters in good to excellent yields with versatile structural diversity. Use of commercially accessible and inexpensive substrates, broad substrate scope and good functional group tolerance are the key features of this protocol.
Copper-catalyzed Pummerer type reaction of α-thio aryl/heteroarylacetates: Synthesis of aryl/heteroaryl α-keto esters
Saha, Pipas,Ray, Sumit Kumar,Singh, Vinod K.
, p. 1765 - 1769 (2017/04/13)
A copper catalyzed Pummerer type reaction of α-thio aryl/heteroarylacetates is described for the first time. This transformation represents a new route to synthesize α-keto esters, which are important intermediates for pharmaceuticals and organic synthesis. The reaction proceeds via in situ generation of a thionium ion that undergoes hydrolysis to furnish α-keto esters in synthetically viable yields (up to 82%).
Alkyl halide-free heteroatom alkylation and epoxidation facilitated by a recyclable polymer-supported oxidant for the in-flow preparation of diazo compounds
Nicolle, Simon M.,Hayes, Christopher J.,Moody, Christopher J.
supporting information, p. 4576 - 4579 (2015/03/18)
Highly reactive metal carbenes, generated from simple ketones via diazo compounds, including diazoamides and -phosphonates, using a recyclable reagent inflow, are transient but versatile electrophiles for heteroatom alkylation reactions and for epoxide formation. The method produces no organic waste, with the only byproducts being water, KI and nitrogen, without the attendant hazards of isolation of intermediate diazo compounds.
Palladium-catalyzed allylic esterification via C-C bond cleavage of a secondary homoallyl alcohol
Wang, Yong,Kang, Qiang
supporting information, p. 4190 - 4193 (2014/10/15)
Palladium-catalyzed allylic esterifications of secondary homoallyl alcohols with acids via sequential retro-allylation and esterification are demonstrated, affording the corresponding allyl ester in up to 99% yield. The electron effect of the substituent of the secondary alcohol was found to be crucial to the selective C-C bond cleavage.
Synthesis of γ,δ-unsaturated quaternary α-alkylamino acids using umpolung reaction and Claisen rearrangement
Mizota, Isao,Tanaka, Katsuki,Shimizu, Makoto
supporting information; experimental part, p. 1847 - 1850 (2012/05/04)
A new synthesis of γ,δ-unsaturated quaternary α-amino acid derivatives was developed utilizing N-alkylation and Claisen rearrangement of allyl α-iminocarboxylates.
Palladium-catalyzed divergent reactions of α-diazocarbonyl compounds with allylic esters: Construction of quaternary carbon centers
Chen, Zi-Sheng,Duan, Xin-Hua,Zhou, Ping-Xin,Ali, Shaukat,Luo, Jian-Yi,Liang, Yong-Min
supporting information; experimental part, p. 1370 - 1374 (2012/03/27)
Take two: α-Diazocarbonyl compounds display a diverse pattern of reactivity upon palladium-catalyzed reaction with esters. Esters bearing an alkynyl group on the carbonyl carbon atom lead to two different C-C bonds at the same carbon atom in a single operation through decarboxylation and migratory insertion, whereas aromatic and benzylic acid derivatives afford aromatic and benzylic esters bearing an O-substituted quaternary carbon center. Copyright
