45708-95-0Relevant academic research and scientific papers
Biomass chitosan-derived nitrogen-doped carbon modified with iron oxide for the catalytic ammoxidation of aromatic aldehydes to aromatic nitriles
Wang, Wei David,Wang, Fushan,Chang, Youcai,Dong, Zhengping
, (2020/11/24)
Nitrogen-doped carbon catalysts have attracted increasing research attention due to several advantages for catalytic application. Herein, cost-effective, renewable biomass chitosan was used to prepare a N-doped carbon modified with iron oxide catalyst (Fe2O3@NC) for nitrile synthesis. The iron oxide nanoparticles were uniformly wrapped in the N-doped carbon matrix to prevent their aggregation and leaching. Fe2O3@NC-800, which was subjected to carbonization at 800 °C, exhibited excellent activity, selectivity, and stability in the catalytic ammoxidation of aromatic aldehydes to aromatic nitriles. This study may provide a new method for the fabrication of an efficient and cost-effective catalyst system for synthesizing nitriles.
Enantioselective Reductive Coupling of Imines Templated by Chiral Diboron
Chen, Dongping,Li, Kaidi,Tang, Wenjun,Xu, Guangqing,Xu, Ronghua,Zhou, Mingkang
supporting information, p. 10337 - 10342 (2020/07/04)
We herein report a general, practical, and highly efficient method for asymmetric synthesis of a wide range of chiral vicinal diamines via reductive coupling of imines templated by chiral diboron. The protocol features high enantioselectivity and stereospecificity, mild reaction conditions, simple operating procedures, use of readily available starting materials, and a broad substrate scope. The method signifies the generality of diboron-enabled [3,3]-sigmatropic rearrangement.
Kinetic Resolution of Secondary Allyl Boronates and Their Application in the Synthesis of Homoallylic Amines
Villar, Laura,Orlov, Nikolai V.,Kondratyev, Nikolay S.,Uria, Uxue,Vicario, Jose L.,Malkov, Andrei V.
supporting information, p. 16262 - 16265 (2018/10/20)
Highly enantioenriched, chromatographically-stable secondary allyl boronates featuring a 1,1,2,2-tetraethyl-1,2-ethanediol fragment (Epin) were obtained by kinetic resolution of their racemic mixtures. The Epin group at boron considerably improved stability of allyl boronates allowing them to be readily isolated by chromatography on silica. The resolved reagents were applied in stereoselective synthesis of homoallylic amines with an internal double bond employing unprotected imines formed in situ from aldehydes and ammonia. The reactions proceeded with an excellent transfer of chirality.
A practical oxidative conversion of aldehydes into N-chloroaldimines
Jin, Can,Wang, Feng,Sun, Bin,Zhuang, Xiaohui
, p. 547 - 551 (2018/11/27)
A novel method for the preparation of N-chloroaldimines from commonly available aromatic aldehydes has been developed. The reaction proceeded effectively by two steps: aldehydes were initially transformed into imines and then chloro-substitution with NaClO2 gave the N-chloroaldimines. This simple protocol allows for the preparation of a variety of aromatic N-chloroaldimines in moderate to excellent yields without the isolation of the imine intermediate. We also found that 3-nitrobenzaldehyde and 4-cyanobenzaldehyde were converted into the related benzonitrile directly under the standard conditions.
Synthesis, photophysical and acidochromic properties of a series of tetrahydrodibenzo[a,i]phenanthridine chromophores
Balijapalli, Umamahesh,Udayadasan, Sathiskumar,Shanmugam, Easwaramoorthi,Kulathu Iyer, Sathiyanarayanan
, p. 233 - 244 (2016/05/24)
A series of luminescent 5-aryl-tetrahydrodibenzo[a,i]phenanthridines was developed through modified synthetic protocol using SnCl2-acetic acid as a catalyst. The synthesis was consistent with various functionalities and significantly improves t
Flexible synthesis of polyfunctionalised 3-fluoropyrroles
Cogswell, Thomas J.,Donald, Craig S.,Marquez, Rodolfo
supporting information, p. 183 - 190 (2015/12/30)
An efficient and selective approach for the synthesis of polyfunctionalised 3-fluoropyrroles has been developed starting from commercial aldehydes. The methodology is concise, efficient and allows for the modular and systematic assembly of polysubstituted 3-fluoropyrroles. This synthesis provides an alternative and highly convergent strategy for the generation of these chemically and biologically important units.
Metal-free, one-pot oxidative conversion of aldehydes to primary thioamides in aqueous media
Yadav, Arvind K.,Srivastava, Vishnu P.,Yadav, Lal Dhar S.
supporting information, p. 408 - 416 (2014/01/06)
One-pot tandem reactions of a variety of aldehydes with aqueous ammonia, molecular iodine, and O,O-diethyl dithiophosphoric acid readily afford the corresponding primary thioamides. This is an inexpensive, practical, and metal-free way of accessing various thioamides from aldehydes in aqueous media. The pure products are obtained simply by filtration followed by successive washing with aqueous sodium thiosulfate and water. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications for the following free supplemental resource(s): Full experimental and spectral details.]
Synthesis, characterization and catalytic activity of dinuclear half-sandwich Ru(II), Rh(III) and Ir(III) complexes
Raja, Nandhagopal,Therrien, Bruno
, p. 1 - 7 (2014/06/09)
The reaction in dichloromethane between the chloro-bridged complexes [(η6-p-iPrC6H4Me) 2Ru2(μ-Cl)2Cl2], [(η5-C5Me5)2Rh 2(μ-Cl)2Cl2] and [(η5-C 5Me5)2Ir2(μ-Cl) 2Cl2], and the ligand precursor, 3,3′-[(1E, 1′E)-{(methylenebis(4,1-phenylene))bis(azanylylidene)}bis(ethan-1-yl-1- ylidene)]bis(4-hydroxy-6-methyl-2H-pyran-2-one) (LH2), has yielded the corresponding neutral dinuclear Ru(II), Rh(III) and Ir(III) complexes of the formula [{(η6-p-iPrC6H4Me)RuCl} 2L] (1), [{(η5-C5Me5)RhCl} 2L] (2) and [{(η5-C5Me5)IrCl} 2L] (3). The complexes were characterized by elemental analysis, infrared, 1H NMR, 13C NMR, ESI mass spectrometry, and complexes 2 and 3 by single-crystal X-ray structure analysis. All complexes were used as catalysts under different reaction conditions for the formation of amides from aldehydes in the presence of NH2OH·HCl and NaHCO3. All complexes show good conversion with catalytic turnover numbers up to 500.
Imine allylation using 2-alkoxycarbonyl allylboronates as an expedient three-component reaction to polysubstituted α-exo-methylene-γ-lactams
Elford, Tim G.,Hall, Dennis G.
body text, p. 6995 - 6998 (2009/04/10)
α-exo-Methylene-γ-lactams are key structural units in a wide variety of biologically active natural products. A concise route to the formation of polysubstituted α-exo-methylene-γ-lactams is described. In this three-component reaction, an imine is formed
Correlation analysis of reactivity in the oxidation of substituted benzylamines by pyridinium hydrobromide perbromide
Garg, Dimple,Goyal, Archana,Kothari, Seema
, p. 935 - 941 (2007/10/03)
The oxidation of benzylamine and twenty-seven ortho-, meta- and para-substituted benzylamines by pyridinium hydrobromide perbromide (PHPB), in dimethylsulphoxide (DMSO), leads to the formation of the corresponding aldimines. The reactions are of first order with respect to both PHPB and the amine. The oxidation of deuterated benzylamine exhibited a substantial kinetic isotope effect (kII/kD = 3.20 at 303 K). An addition of pyridinium bromide does not affect the rate. PHPB itself has been postulated as the reactive oxidizing species. The rates of the oxidation of para- and meta-substituted benzylamines were correlated with Taft's and Swain's field and resonance substituent constants. The oxidation of para-substituted benzylamines showed an excellent correlation with Taft's σI and σRBA values; the meta-compounds correlated best with σI and σR0 values. Rates of the ortho-substituted compounds showed a significant correlation with Charton's triparametric equation. Suitable mechanism has been proposed.
