1624-46-0Relevant academic research and scientific papers
Organoborane reagents in the C-alkylation of aromatic aldimines
Valpuesta, Maria,Munoz, Carmen,Diaz, Amelia,Suau, Rafael,Torres, Gregorio
, p. 4467 - 4470 (2007)
The reaction of an aldimine with dicyclohexylboron chloride in the presence of hydrogen peroxide gives N-[cyclohexyl(aryl)methyl]arylamines 2 in good yields via oxidized imine-borane complexes. The amines can also be obtained by a three-component reaction
A novel water-dispersible and magnetically recyclable nickel nanoparticles for the one-pot reduction-Schiff base condensation of nitroarenes in pure water
Ghamari Kargar, Pouya,Ravanjamjah, Asiye,Bagherzade, Ghodsieh
, p. 1916 - 1933 (2021/07/10)
In this work, a heterogeneous nanocatalyst called Ni-Fe3O4@Pectin~PPA ~ Piconal was first synthesized, which was investigated as a bifunctional catalyst containing nickel functional groups. On the other hand, this Ni-Fe3O4@Pectin~PPA ~ Piconal catalyst in aqueous solvents shows a very effective performance at ambient temperature for the nitroarene reduction reaction with sodium borohydride, for which NaBH4 is considered as a reducing agent. This is a novelty magnetic catalyst that was approved by various methods, including Fourier-transform infrared spectroscopy (FT-IR), X-ray powder diffraction (XRD), Dynamic light scattering (DLS), Transmission electron microscopy (TEM), vibrating sample magnetometer (VSM), Inductively coupled plasma (ICP), Energy-dispersive X-ray spectroscopy (EDX), and Field emission scanning electron microscopy (FESEM) analyses. From the satisfactory results obtained from the reduction of nitrogen, this catalytic system is used for a one-pot protocol containing a reduction-Schiff base concentration of diverse nitroarenes. It was corroborated with the heterogeneous catalytic experiments on the one-pot tandem synthesis of imines from nitroarenes and aldehydes. Finally, the novel Ni-Fe3O4@Pectin~PPA ~ Piconal catalyst could function as a more economically desirable and environmentally amicable in the catalysis field. The favorable products are acquired in good to high performance in the attendance of Ni-Fe3O4@Pectin~PPA ~ Piconal as a bifunctional catalyst. This catalyst can be recycled up to six steps without losing a sharp drop.
Catalytic Asymmetric γ-Lactam Synthesis from Enolisable Anhydrides and Imines
Collar, Aarón Gutiérrez,Trujillo, Cristina,Lockett-Walters, Bruce,Twamley, Brendan,Connon, Stephen J.
, p. 7275 - 7279 (2019/05/15)
An anion-binding approach to the problem of preparing enantioenriched γ-lactams from enolisable anhydrides and imines is reported. A simple bisurea catalyst promotes the cycloaddition between α-aryl succinic anhydrides and either PMP- or benzhydryl-protec
Improving C=N bond reductions with (Cyclopentadienone)iron complexes: Scope and limitations
Cettolin, Mattia,Bai, Xishan,Lübken, Dennis,Gatti, Marco,Facchini, Sofia Vailati,Piarulli, Umberto,Pignataro, Luca,Gennari, Cesare
supporting information, p. 647 - 654 (2018/10/24)
Herein, we broaden the application scope of (cyclo-pentadienone)iron complexes 1 in C=N bond reduction. The catalytic scope of pre-catalyst 1b, which is more active than the “Kn?lker complex” (1a) and other members of its family, has been expanded to the catalytic transfer hydrogenation (CTH) of a wider range of aldimines and ketimines, either pre-isolated or generated in situ. The kinetics of 1b-promoted CTH of ketimine S1 were assessed, showing a pseudo-first order profile, with TOF = 6.07 h–1 at 50 % conversion. Moreover, the chiral complex 1c and its analog 1d were employed in the enantioselective reduction of ketimines and reductive amination of ketones, giving fair to good yields and moderate enantioselectivity.
Phosphine-Free Well-Defined Mn(I) Complex-Catalyzed Synthesis of Amine, Imine, and 2,3-Dihydro-1 H-perimidine via Hydrogen Autotransfer or Acceptorless Dehydrogenative Coupling of Amine and Alcohol
Das, Kalicharan,Mondal, Avijit,Pal, Debjyoti,Srivastava, Hemant Kumar,Srimani, Dipankar
supporting information, p. 1815 - 1825 (2019/04/30)
The application of nontoxic, earth-abundant transition metals in place of costly noble metals is a paramount goal in catalysis and is especially interesting if the air- and moisture-stable ligand scaffold is used. Herein, we report the synthesis of amines/imines directly from alcohol and amines via hydrogen autotransfer or acceptorless dehydrogenation catalyzed by well-defined phosphine-free Mn complexes. Both imines and amines can be obtained from the same set of alcohols and amines using the same catalyst, only by tuning the reaction conditions. The amount and nature of the base are found to be a highly important aspect for the observed selectivity. Both the primary and secondary amines have been employed as substrates for the N-alkylation reaction. As a highlight, we showed the chemoselective synthesis of resveratrol derivatives. Furthermore, the Mn-catalyzed dehydrogenative synthesis of structurally important 2,3-dihydro-1H-perimidines has also been demonstrated. Density functional theory calculations were also carried out to model the reaction path and to calculate the reaction profile.
Iron-Catalyzed Reductive Ethylation of Imines with Ethanol
Vayer, Marie,Morcillo, Sara P.,Dupont, Jennifer,Gandon, Vincent,Bour, Christophe
supporting information, p. 3228 - 3232 (2018/03/13)
The borrowing hydrogen strategy has been applied to the ethylation of imines with an air-stable iron complex as precatalyst. This approach opens new perspectives in this area as it enables the synthesis of unsymmetric tertiary amines from readily available substrates and ethanol as a C2 building block. A variety of imines bearing electron-rich aryl or alkyl groups at the nitrogen atom could be efficiently reductively alkylated without the need for molecular hydrogen. The mechanism of this reaction, which shows complete selectivity for ethanol over other alcohols, has been studied experimentally and by means of DFT computations.
Quinone-catalyzed oxidative deformylation: Synthesis of imines from amino alcohols
Liu, Xinyun,Phan, Johnny H.,Haugeberg, Benjamin J.,Londhe, Shrikant S.,Clift, Michael D.
supporting information, p. 2895 - 2901 (2018/01/17)
A new method for imine synthesis by way of quinone-catalyzed oxidative deformylation of 1, 2-amino alcohols is reported. A wide range of readily accessible amino alcohols and primary amines can be reacted to provide N-protected imine products. The methodology presented provides a novel organocatalytic approach for imine synthesis and demonstrates the synthetic versatility of quinone-catalyzed oxidative C-C bond cleavage.
Effects of molecular conformation on the spectroscopic properties of 4,4′-disubstituted benzylideneanilines
Fang, Zhengjun,Wu, Feng,Yi, Bing,Cao, Chenzhong,Xie, Xin
, p. 52 - 57 (2015/10/29)
The relationship between the molecular conformation and spectroscopic properties of unsymmetrical 4,4′-disubstituted benzylideneanilines, was explored by the combination of experiment and reference data. Crystal structure information and spectroscopic beh
Ruthenium-catalyzed double-fold C-H tertiary alkoxycarbonylation of arenes using di-tert-butyl dicarbonate
Hong, Xiaohu,Wang, Hao,Liu, Bingxin,Xu, Bin
supporting information, p. 14129 - 14132 (2014/12/11)
An efficient ruthenium-catalyzed double-fold C-H alkoxycarbonylation of arenes was developed using di-tert-butyl dicarbonate as the tertiary esterification reagent, which leads to a direct route to valuable 2,6-dicarboxylated products. This journal is
Cobalt-catalyzed arylation of aldimines via directed C-H bond functionalization: Addition of 2-arylpyridines and self-coupling of aromatic aldimines
Gao, Ke,Yoshikai, Naohiko
supporting information; body text, p. 4305 - 4307 (2012/05/20)
A cobalt-N-heterocyclic carbene catalyst, in combination with an appropriate Grignard reagent, promotes a chelation-assisted aromatic C-H functionalization reaction via addition to an aromatic aldimine. The Royal Society of Chemistry 2012.
