23652-86-0Relevant academic research and scientific papers
Highly efficient and facile synthesis of β-enaminones catalyzed by diphenylammonium triflate
Zhao, Ting-Ting,Song, Jiang-Long,Hong, Feng-Qing,Xia, Jian-Sheng,Li, Jian-Jun
, p. 2857 - 2868 (2019/08/21)
Abstract: The catalytic performance of diphenylammonium triflates as an organocatalyst in the synthesis of β-enaminones from various substituted β-diketones and amides (or amines) were evaluated. A wide range of β-enaminones were efficiently synthesized in good to excellent yields under mild reaction conditions. Applying diphenylammonium triflate (DPAT) as catalyst makes this protocol cost-effective, low corrosive and easy to handle. Graphic abstract: [Figure not available: see fulltext.].
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.
Electrochemical behaviour of amino substituted β-amino α,β-unsaturated ketones: A computational chemistry and experimental study
Ngake, Tankiso Lawrence,Potgieter, Johannes Hermanus,Conradie, Jeanet
, p. 1070 - 1082 (2019/01/05)
The synthesis, identification and electrochemical properties are reported here, for a series of five novel and seven known amino substituted β-amino α,β-unsaturated ketones (bidentate N,O-ligands) of the type CH3COCHC(NHR)CH3, where R = H, Ph, CH2Ph, CH(CH3)2, p-CF3-Ph or p-tBu-Ph (Series 1), as well as type PhCOCHC(NHR)CH3, where R = H, Ph, p-NO2-Ph, 3,5-di-Cl-Ph, 2-CF3-4-Cl-Ph, and also PhCOCHC(NHPh)CF3 (Series 2). The cyclic voltammograms measured in CH3CN, generally exhibit both a chemically and electrochemically irreversible reduction peak between ?1.2 V and ?3.1 V vs FcH/FcH+, producing an unstable radical anion, for most of these 1,3-amino ketones. Only ligands PhCOCHC(NHPh)CH3, PhCOCHC(NHPh)CF3 and PhCOCHC(NH(p-NO2-Ph))CH3, showed reversible electrochemical behaviour, at higher scan rates. Density functional theory (DFT) calculations proved the unpaired spin density in the radical anion to be distributed over the pseudo-aromatic O–C–C–C–N backbone of the 1,3-amino ketones, extending further over the phenyl rings of the phenyl-containing ligands. Various DFT calculated energies, such as the energy of the lowest unoccupied molecular orbital (the orbital into which the electron is added upon reduction), as well as the DFT calculated gas phase adiabatic electron affinities, relate linearly to the experimentally measured reduction potential. These obtained linear relationships confirmed that good communication via conjugation exists, between the R substituent on the amino group and the rest of the 1,3-amino ketone.
Sublimable bis(β-iminoenolate)palladium(II) complexes and their application as catalysts in Suzuki-Miyaura reactions
Kim, Mi Jin,Jung, Myung Jin,Kim, Yeong Joon,Sung, Ha Kyoung,Lee, Ju Young,Ham, Sung Jin,Park, Chan Pil
supporting information, p. 2989 - 2993 (2018/07/02)
The Pd(II) complexes strongly chelated by two β-iminoenolate ligands were easily synthesized in only two steps, and purified based on their sublimable and highly stable property. The Pd(II) complexes anchored on a silica surface showed good catalytic activity in Suzuki-Miyaura reactions (up to 99% yield with 0.05 mol% catalyst). They tolerated a wide range of temperature (rt～110 °C) and various solvents, and could be reused multiple times after simple recovering process.
Iron-Catalyzed Synthesis of Substituted Thiazoles from Enamines and Elemental Sulfur through C?S Bond Formation
Wu, Mingzhong,Jiang, Yong,An, Zhenyu,Qi, Zhenjie,Yan, Rulong
supporting information, p. 4236 - 4240 (2018/09/20)
An atom economical approach for the synthesis of substituted thiazoles starting from enamines and elemental sulfur through the C?H functionalization/C?S bond formation is described. Under the optimized conditions, various substituted enamines reacted smoothly with elemental sulfur and the desired substituted thiazoles were generated in moderate to excellent yields. (Figure presented.).
Microwave-assisted palladium-catalyzed allylation of β-enaminones
Erray, Imen,Rezgui, Farhat,Oble, Julie,Poli, Giovanni
supporting information, p. 2196 - 2200 (2014/11/12)
A new palladium-catalyzed approach for the C-allylation of β-enaminones under microwave irradiation is reported. This methodology provides an easy access to a variety of α-allylated enaminones. The reaction takes place with the preservation of the enamine function, which is poised for further transformations towards nitrogen-containing heterocycles. Georg Thieme Verlag Stuttgart New York.
Zn[aminoacid]2 hybrid materials applied as heterogeneous catalysts in the synthesis of β-enaminones
Winck, Cristiane R.,Darbem, Mariana P.,Gomes, Roberto S.,Rinaldi, Andrelson W.,Domingues, Nelson Luís C.
supporting information, p. 4123 - 4125 (2014/07/22)
Hybrid materials have seized attention from scientific community mainly as heterogenic catalysts in organic reactions on a large scale succeeding in some organic compounds with high yields. One of the most important classes of hybrid materials used for this purpose involves the complexation of Zn and aminoacids. Herein, we introduced Zn[Pro]2 and Zn[Gly]2 in the synthesis of several β-enaminones via solvent free protocol and using an ultrasound device.
Zn[aminoacid]2 hybrid materials applied as heterogeneous catalysts in the synthesis of β-enaminones
Winck, Cristiane R.,Darbem, Mariana P.,Gomes, Roberto S.,Rinaldi, Andrelson W.,Domingues, Nelson Luís C.
supporting information, p. 4123 - 4125 (2015/02/02)
Hybrid materials have seized attention from scientific community mainly as heterogenic catalysts in organic reactions on a large scale succeeding in some organic compounds with high yields. One of the most important classes of hybrid materials used for this purpose involves the complexation of Zn and aminoacids. Herein, we introduced Zn[Pro]2 and Zn[Gly]2 in the synthesis of several β-enaminones via solvent free protocol and using an ultrasound device.
H2O2-promoted reactions of aliphatic primary amines with 1,3-diketones for the synthesis of 1 H -pyrrol-3(2 H)-ones at ambient temperature in water
Sun, Xi,Li, Pinhua,Zhang, Xiuli,Wang, Lei
supporting information, p. 2126 - 2129 (2014/05/06)
A green organic reaction of aliphatic primary amines with 1,3-diketones promoted by 30% aqueous H2O2 has been developed. It provides an inexpensive, regioselective, and efficient approach to 1H-pyrrol-3(2H)-ones with high yields from the simple and readily available starting materials in one pot via multicomponent tandem cyclization reactions and C-C cleavage under very mild and environmentally friendly reaction conditions.
A metal-free multicomponent cascade reaction for the regiospecific synthesis of 1,5-disubstituted 1,2,3-triazoles
Cheng, Guolin,Zeng, Xiaobao,Shen, Jinhai,Wang, Xuesong,Cui, Xiuling
supporting information, p. 13265 - 13268 (2014/01/06)
About specifics: A method for the regiospecific synthesis of the title compounds through an unprecedented Michael addition/deacylative diazo transfer/cyclization sequence has been established. The simple and practical method can be used for the modification of primary amines including chiral α-amines. The process involves the formation three covalent bonds and the cleavage of two covalent bonds (see scheme, Ts=4-toluenesulfonyl).
