18632-42-3Relevant academic research and scientific papers
Electrochemically Induced Intermolecular Cross-Dehydrogenative C-O Coupling of β-Diketones and β-Ketoesters with Carboxylic Acids
Bityukov, Oleg V.,Matveeva, Olesya K.,Vil, Vera A.,Kokorekin, Vladimir A.,Nikishin, Gennady I.,Terent'Ev, Alexander O.
, p. 1448 - 1460 (2019/02/07)
The electrochemically induced cross-dehydrogenative C-O coupling of β-diketones and β-ketoesters (C-H reagents) with carboxylic acids (O-H reagents) was developed. An important feature of this reaction lies in the selective formation of intermolecular C-O
Copper-Catalysed (Diacetoxyiodo)benzene-Promoted Aerobic Esterification Reaction: Synthesis of Oxamates from Acetoacetamides
Zhang, Zhiguo,Gao, Xiaolong,Yu, Haifeng,Zhang, Guisheng,Liu, Jianming
supporting information, p. 3406 - 3411 (2018/07/31)
A copper-catalysed (diacetoxyiodo)benzene-promoted aerobic esterification reaction of acetoacetamides was developed for the synthesis of oxamates, which are useful precursors in synthetic organic chemistry. This practical and mild synthetic approach proceeded at 25 °C under open-air conditions and afforded methyl 2-oxo-2-(phenylamino)acetates in good to excellent yields combined with C?C σ-bond cleavage and formal oxidative C?H bond functionalization. A mechanism is proposed. (Figure presented.).
Apparent electrophilic fluorination of 1,3-dicarbonyl compounds using nucleophilic fluoride mediated by PhI(OAc)2
Nash, Toby J.,Pattison, Graham
supporting information, p. 3779 - 3786 (2015/06/16)
The apparent electrophilic fluorination of 1,3-dicarbonyl compounds using Et3N·3HF as a nucleophilic fluoride source is reported. This reaction requires PhI(OAc)2 as oxidant and can be conducted safely in standard laboratory glassware. Alternative selectivity compared to Selectfluor was observed in some cases. This approach may reduce our reliance on difficult-to-handle fluorine gas and expensive electrophilic fluorinating agents derived from elemental fluorine. Mechanistic analysis related to the active fluorinating species and fluoride/acetate exchange is presented. The apparent electrophilic fluorination of 1,3-dicarbonyl compounds using Et3N·3HF mediated by the in-situ formation of PhIF2 from PhI(OAc)2 is reported. This can be performed safely in standard laboratory glassware, and this approach may reduce our reliance on difficult-to-handle fluorine gas and expensive electrophilic fluorinating agents derived from elemental fluorine.
A copper-catalyzed formal O-H insertion reaction of α-diazo-1,3- dicarbonyl compounds to carboxylic acids with the assistance of isocyanide
Wang, Zikun,Bi, Xihe,Liang, Yongjiu,Liao, Peiqiu,Dong, Dewen
supporting information, p. 3976 - 3978 (2014/04/03)
A novel copper-catalyzed formal O-H insertion of α-diazo-1,3- dicarbonyl compounds to carboxylic acids has been developed, providing a straightforward synthetic method for α-acyloxy-1,3-dicarbonyl compounds, in which the activation of carboxylic acids by isocyanide plays a crucial role.
Various α-oxygen functionalizations of β-dicarbonyl compounds mediated by the hypervalent iodine(III) reagent p-iodotoluene difluoride with different oxygen-containing nucleophiles
Jun, Yu,Jun, Tian,Chi, Zhang
experimental part, p. 531 - 546 (2010/06/13)
p-Iodotoluene difluoride (p-Tol-IF2) has been found to be a general reagent for the effective introduction of various oxygen-containing functionalities including tosyloxy, mesyloxy, acetoxy, phosphoryloxy, methoxy, ethoxy and isopropoxy at the α-position of β-dicarbonyl compounds. These transformations can be readily realized by the use of the combined reagent of p-iodotoluene difluoride and various oxygen-containing nucleophilic compounds such as p-toluenesulfonic acid, methanesulfonic acid, acetic acid, diphenyl phosphate, methanol, ethanol and propan-2-ol under mild conditions, respectively. And, the in situ generated hypervalent iodine(III) species via ligand exchange between p-iodotoluene difluoride and the respective oxygen-containing nucleophiles are believed to be the real oxidizing agents in such transformations.
A convenient synthesis of pyridine and 2,2′-bipyridine derivatives
Altuna-Urquijo, Marta,Gehre, Alexander,Stanforth, Stephen P.,Tarbit, Brian
experimental part, p. 975 - 984 (2009/04/10)
α-Chloro-α-acetoxy-β-keto-esters 9 were readily prepared from β-keto-esters 6 in good overall yields. These compounds reacted as α,β-diketo-ester equivalents 2 with amidrazones 1 yielding triazines 3, generally in good yields. Picolinates 10 provided an alternative source of α,β-diketo-ester equivalents 2 when treated with copper(II) acetate. A 'one-pot' reaction of the α,β-diketo-ester equivalents 2 with amidrazones 1 in the presence of 2,5-norbornadiene 5 in boiling ethanol yielded the pyridines 4 and 2,2′-bipyridines 4 (R1=2-pyridyl) directly without the need to isolate the corresponding triazines 3. Triazine 3c reacted with the aza-dienophiles 13 and 17 affording the products 16 and 18, respectively, in good yields.
THE DEGRADATION OF CARBOXYLIC ACIDS INTO ALDEHYDES. REGIOSELECTIVE α-ACETOXYLATION OF 1,2,4-TRIAZOLIUM SALTS WITH DIACETOXYIODATE(1)ANION
Doleschall, Gabor,Toth, Gabor
, p. 1649 - 1666 (2007/10/02)
A novel method was developed for degradation of carboxylic acid into aldehydes containing one C atom less whose key step consists in α-acetoxylation of 5-alkyl-3-methylthio-1,4-diphenyl-1,2,4-triazolium iodides by (diacetoxyiodo)benzene.The mechanism of the regioselective α-acetoxylation was studied and the diacetoxy-iodate(1)anion was shown to be the actual oxidising agent.Further oxidation reactions of tetraethylammonium diacetoxyiodate(1) were investigated.A novel method was developed for the oxidation of primary alkyl amines into aldehydes by the novel heterocyclic reagent 5-bromo-3-methylthio-1,4-diphenyl-1,2,4-triazolium bromide and diethyl azodicarboxylate.
Facile Entry into the 7-Oxo-4-oxa-1-azabicyclohept-2-ene Ring System
Cuffe, John,Porter, Alexander E. A.
, p. 1257 - 1258 (2007/10/02)
Rhodium(II) acetate-catalysed addition of ethyl diazoacetoacetate to (+/-)-4-acetoxyazetidin-2-one results in the formation of ethyl 7-oxo-4-oxa-1-azabicyclohept-2-ene-2-carboxylate.
