52909-66-7Relevant articles and documents
Redox Property of Enamines
Li, Yao,Wang, Dehong,Zhang, Long,Luo, Sanzhong
, p. 12071 - 12090 (2019/10/11)
Enamines are electron-rich compounds bearing intriguing redox properties. Herein, a series of secondary enamines condensed from primary amine and β-ketocarbonyls were synthesized and their electrochemical oxidation properties were systematically studied by cyclic voltammetry. Furthermore, theoretical calculation of oxidation potentials of enamines, particularly those catalytic intermediates, was also conducted to further broaden the scope investigated. Possible structural factors on oxidation and the nature of the resulted radical cation intermediates were revealed and discussed. Correlation of redox potentials with molecular properties such as highest occupied molecular orbital energies and natural population analysis charge were explored, and there appears no simple linear correlation. On the other hand, a good correlation with Mayr's nucleophilicity parameter N was noted among a range of catalytically relevant enamines. Spin population analysis disclosed that enamine radical cations mainly exhibit the carbon-center free radical feature. Taking experimental and computation data together, a comprehensive picture about the redox property of enamines is presented, which would provide guidance in the development of oxidative enamine catalysis and transformations.
Visible Light Promoted β-C—H Alkylation of β-Ketocarbonyls via a β-Enaminyl Radical Intermediate
Wang, Dehong,Zhang, Long,Luo, Sanzhong
, p. 311 - 320 (2018/02/21)
A 5πe carbonyl activation mode is reported on the basis of photo-induced single-electron-transfer (SET) oxidation of a secondary enamine. The resultant β-enaminyl radical intermediate was trapped by a wide range of Michael acceptors, producing β-alkylation products of β-ketocarbonyls in a highly efficient manner.
Cyanuric chloride catalysed rapid conversion of β-ketoesters into β-enaminoesters under mild and solvent-free conditions
Kamble,Joshi,Atkore
experimental part, p. 616 - 621 (2012/07/03)
Cyanuric chloride is shown to be an extremely efficient catalyst for the synthesis of β-enaminoesters from β-ketoesters under solvent-free conditions by grinding in a mortar with pestle at 25 °C. A short reaction time, an inexpensive and easily available catalyst, mild reaction conditions and excellent yields of the products are attractive features of this methodology.
Stereodefined homopropargyl amines by tandem nucleophilic addition/fragmentation of dihydropyridone triflates
Tummatorn, Jumreang,Dudley, Gregory B.
supporting information; experimental part, p. 158 - 160 (2011/03/20)
Dihydropyridone (DHPD) triflates undergo nucleophile-triggered fragmentation to provide homopropargyl amine derivatives, the stereochemistry of which is defined by starting from readily available β-amino esters.
Ni(OAc)2: A highly efficient catalyst for the synthesis of enaminone and enamino ester derivatives under solvent-free conditions
Liu, Ju-Yan,Cao, Gai-E.,Xu, Wei,Cao, Jie,Wang, Wei-Lu
experimental part, p. 685 - 691 (2010/11/20)
Ni(OAc)2 was found to be an efficient catalyst for the synthesis of β-enamino ketones or esters from β-dicarbonyl compounds and amines under solvent-free conditions. The reusability of the catalyst was successfully examined without noticeable loss of its catalytic activity. Copyright
P2O5/SiO2 as a new, efficient, and reusable catalyst for preparation of β-enaminones under solvent-free conditions
Mohammadizadeh, Mohammad R.,Hasaninejad,Bahramzadeh,Khanjarlou, Z. Sardari
experimental part, p. 1152 - 1165 (2009/10/09)
P2O5/SiO2 (30% w/w) was applied as an efficient, heterogeneous, and reusable catalyst for the synthesis of β-enaminones. The reactions were rapidly completed at 80°C under solvent-free conditions and products were obtained in good to excellent yields. Copyright Taylor & Francis Group, LLC.
General, mild and efficient synthesis of β-enaminones catalyzed by ceric ammonium nitrate
Sridharan, Vellaisamy,Avenda?o, Carmen,Menéndez
, p. 881 - 884 (2008/02/02)
Ceric ammonium nitrate catalyzes the reaction between aromatic or aliphatic primary amines and a variety of β-dicarbonyl compounds, including β-ketoesters, β-ketothioesters and β-diketones. The reaction proceeds smoothly at room temperature in short react
Enamination of 1,3-dicarbonyl compounds catalyzed by tin tetrachloride
Zhang, Zhan-Hui,Ma, Zi-Chuan,Mo, Li-Ping
, p. 535 - 539 (2008/09/18)
Tin tetrachloride has been found to be an extremely efficient catalyst for the enamination of 1,3-dicarbonyl compounds under solvent-free conditions at room temperature.
Phosphotungstic acid catalysed synthesis of β-enamino compounds under solvent-free conditions
Li, Geng-Chen
, p. 696 - 698 (2008/09/20)
A convenient eco-friendly procedure has been developed for the synthesis of β-enaminones and β-enamino esters by reacting 1,3-dicarbonyl compounds with amines in the presence of catalytic amounts of phosphotungstic acid (H3PW12O40,1 mol%). The reaction proceeds smoothly at room temperature under solvent-free conditions and gives the corresponding β-enamino compounds in high to excellent yields.
ZrCl4-catalyzed efficient synthesis of enaminones and enamino esters under solvent-free conditions
Lin, Jin,Zhang, Li-Feng
, p. 77 - 81 (2007/10/03)
A facile synthesis of β-enaminones and enamino esters by condensation of β-dicarbonyl compounds with differently substituted amines in the presence of ZrCl4 under solvent-free conditions is reported.
