14545-01-8Relevant academic research and scientific papers
Coordination compound containing 1,10-phenanthroline-shaped N-heterocyclic carbene copper (I), and application thereof
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Paragraph 0014, (2018/07/30)
The invention discloses a coordination compound containing 1,10-phenanthroline-shaped N-heterocyclic carbene copper (I) (as well as a coordinate compound monocrystal), and application thereof. The coordination compound containing the 1,10-phenanthroline-s
“Zero VOC” Synthetic Strategy – Aromatic Amination Reactions in Deep Eutectic Solvents
Valvi, Arun,Tiwari, Shraeddha
, p. 4933 - 4939 (2018/09/11)
Rising concern for environment hazards resulting from the use of volatile organic compounds (VOCs) is prompting many chemists to use “green” solvents like water, polyethylene glycol, ionic liquids and deep eutectic solvents (DES). With a few notable exceptions, many of these processes still need to use volatile organic solvents for the workup and isolation of products. In the present report, we demonstrate a “zero VOC” protocol which eliminates the need to use organic solvents for any stage of the reaction. As a proof of concept, nucleophilic aromatic substitution reactions of 1-halo-2,4-dinitrobenzene with secondary amines were carried out in deep eutectic solvents. The reaction workup involved the addition of water for separating the product from the DES. Evaporation of water led to recovery of the DES, which exhibited good recyclability. The reaction in deep eutectic solvents was much faster than that in many other solvents, as confirmed by the kinetic studies. An attempt was made to elucidate the origin of this rate enhancement based on analysis activation parameters and correlation with the polarity parameters. The results show that use of deep eutectic solvents can take chemists a step closer towards the “zero VOC” synthetic strategy.
Direct N-arylation of azaheterocycles with aryl halides under ligand-free condition
Yang, Qichao,Wang, Yufang,Zhang, Baoji,Zhang, Mingjie
, p. 2389 - 2393,5 (2020/09/16)
A simple and efficient Ci￡N cross-coupling method of aryl halides with various heterocycles was reported, by using 10 mol% of CuI as catalyst and 1.2 equiv. NaH as base. Aryl iodides, aryl bromides and many substituted aryl chlorides could efficiently react with heterocycles, providing variety of N-arylated products in good to excellent yields. The ligand-free catalyst system was stable in air and could be readily reused. An efficient, convenient and applicable method was developed for the N-arylation of azaheterocycles catalyzed by CuI and NaH under ligand free condition. Copyright
The Reaction of Imidazole with some 1-Halogeno-2,4-dinitrobenzenes in Aprotic Solvents
Akinyele, Elizabeth T.,Crist, Delanson F.,Hirst, Jack
, p. 905 - 909 (2007/10/02)
The reactions of imidazole with 1-chloro- and 1-fluoro-2,4-dinitrobenzenes in dimethyl sulfoxide are not catalysed by imidazole, DABCO or imidazolium perchlorate.In acetonitrile these reactions are not catalysed by the nucleophile or DABCO but the second-
REACTIVITY OF NUCLEOPHILES IN DIMETHYL SULFOXIDE AND ITS COMPARISON WITH NUCLEOPHILIC REACTIVITY IN PROTIC MEDIUM
Zima, Vitezslav,Pytela, Oldrich,Kavalek, Jaromir,Vecera, Miroslav
, p. 2715 - 2720 (2007/10/02)
Reactions of 2,4-dinitrophenyl acetate and 2,4-dinitrofluorobenzene as model substrates with 12 nucleophiles have been studied in dimethyl sulfoxide.The rate constants obtained have been discussed with regard to the nucleophilic reactivity differences in dimethyl sulfoxide and protic solvents inclusive of the different manifestations of the charge of nucleophiles.The applicability of an earlier-suggested correlation equation to the data obtained has been verified.The reaction medium markedly affects the reactivity of nucleophiles, the effect of charge being substantially greater in aprotic solvents (electrostatic interaction) than in protic ones (solvation).In spite of these differences the correlation with application of an empirical nucleophilicity scale suggested earlier is satisfactory, the regression coefficients obtained reflect changes in the nature of medium.
Kinetic Study of the Reaction of N-(2,4-Dinitrophenyl)imidazole with Piperidine and n-Butylamine
Vargas, Elba B. de,Rossi, Rita H. de
, p. 3978 - 3983 (2007/10/02)
The reaction of N-(2,4-dinitrophenyl)imidazole, 1, with piperidine and n-butylamine was studied.The reaction with piperidine is catalyzed by hydroxide ions and by the amine while the reaction with n-butylamine is weakly catalyzed by hydroxide ion.The hydrolysis of the substrate competes with the aminolysis reaction.The base catalysis in the reaction of 1 with piperidine is shown to be a consequence of rate-limiting deprotonation of the zwitterionic intermediate complex, followed by spontaneous (noncatalyzed) leaving group expulsion.On the other hand, the small rateacelaration observed in the reaction of butylamine as well as the catalysis of the hydrolysis reaction by n-butylamine and piperidine is considered of unclear origin.
1,2,4-TRINITROBENZENE AS A THIOL REAGENT
Takahashi, Seitaro,Kokubo, Masayuki,Satake, Kazuo
, p. 1445 - 1448 (2007/10/02)
The 2,4-dinitrophenylation of thiol or amino group with 1,2,4-trinitrobenzene proceeded quantitatively at pH 8.5 and 30 deg C.The rate of S-dinitrophenylation was ca. 1E4 times faster than that of N-dinitrophenylation.So this reaction can be used for both the determination of thiol even in the presence of large excess amine and the specific modification of thiol in proteins.
