39159-65-4Relevant articles and documents
A Reusable CNT-Supported Single-Atom Iron Catalyst for the Highly Efficient Synthesis of C?N Bonds
Baell, Jonathan B.,Ding, Qifeng,Huang, Fei,Huang, He,Xu, Mingjie,Yu, Yang,Zhang, Lihui,Zheng, Jian-Guo
supporting information, (2020/03/24)
C?N bond formation is regarded as a very useful and fundamental reaction for the synthesis of nitrogen-containing molecules in both organic and pharmaceutical chemistry. Noble-metal and homogeneous catalysts have frequently been used for C?N bond formatio
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.
Formic acid: A low-cost, mild, ecofriendly, and highly efficient catalyst for the rapid synthesis of β-enaminones
Patil, Siddappa A.,Medina, Phillip A.,Gonzalez-Flores, Diego,Vohs, Jason K.,Dever, Seth,Pineda, Leslie W.,Montero, Mavis L.,Fahlman, Bradley D.
, p. 2349 - 2364 (2013/07/26)
β-Enaminones have been synthesized by the condensation reaction of b-diketones with various anilines in the presence of a catalytic amount of formic acid, mild and highly efficient acid catalyst in methanol. These condensation reactions proceed smoothly in short reaction times with near-quantitative yields. Copyright
