Electrochemical carboxylation of fluorocontaining imines with preparation of fluorinated N-phenylphenylglycines

Koshechko, V. G.; Titov, V. E.; Bondarenko, V. N.; Pokhodenko, V. D.

doi:10.1016/j.jfluchem.2008.06.010

Cited by 46 publications

(31 citation statements)

References 29 publications

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“…Our mass spectrometric studies of other derivatives of N-phenylphenylglycine [5] using different targets gave results similar to those obtained for N-phenyl-p-fluorophenylglycine. In particular, the selection of conditions for obtaining the peak for the monomolecular ion of N-p-fluorophenyl-p-fluorophenylglycine (2) was most difficult among the fluorine-containing amino acids studied.…”

Section: Resultssupporting

confidence: 81%

“…In previous work [4,5], we were the first to show that the electrochemically-activated introduction of carbon dioxide into fluorine-containing aromatic imines may lead to the formation of fluorine-containing N-phenylphenylglycine derivatives, which opens new possibilities for obtaining amino acids. In order to confirm the structure of the fluorine-containing amino acids, we attempted to use mass spectrometry along with NMR spectroscopy.…”

mentioning

confidence: 99%

“…In the present study, we used fluorine-containing amino acids, namely, N-phenylphenylglycine derivatives obtained according to our previous work [5].…”

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confidence: 99%

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Effect of the target on the efficiency of generation of monomolecular ions of fluorine-containing amino acids in laser desorption/ionization

et al. 2009

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A comparative analysis was carried out on the laser desorption/ionization (LDI) mass spectra of fluorine derivatives of N-phenylphenylglycine using different targets. The extent of generation of molecular ions of the fluorine-containing amino acids was shown to depend significantly on the nature of the target surface. Alkali metal chlorides (LiCl, NaCl, KCl, and CsCl) have the highest efficiency among the targets studied (standard metal target, polished monocrystalline silicon, glass, silica) in the generation of molecular ions of fluorine-containing amino acids, which increases in the series LiCl < NaCl < KCl < CsCl.The study of the structure of amino acids, their identification and analysis by traditional mass spectrometric methods often provide little information and are sometimes infeasible due to the significant decomposition of such molecules upon ionization [1]. Mass spectrometric methods, which permit us to avoid the "hard" ionization of unstable molecules such as laser-activated mass spectrometry, hold the greatest promise for the study of such molecules. Variation of the laser energy permits optimization of the relative intensity of the ions detected. Thus, the commonly used MALDI method (matrix assisted laser desorption ionization) is based on the laser irradiation of the compound studied cocrystallized with another compound called the matrix, which often facilitates ionization and the transfer of the compound studied to the gaseous phase. As a rule, organic acids having maximum laser radiation absorption at about 337 nm are most commonly used as matrices [2]. The use of the MALDI method for studying amino acids (and frequently, other organic compounds with low and medium mass up to 500 Da) is quite limited due to the overlap of peaks related to the matrix and the peaks of the compound studied. On the other hand, expansion of the arsenal of the laser desorption method permits us to obtain additional possibilities in the study of organic compounds with different composition and structure [3]. The major advantage using this method is found in the generation of monomolecular ions and mass spectra containing a small amount of organic molecule fragments with low and medium mass without using a matrix. This method makes possible not only the detection of short-lived monomolecular ions but also the study 180 0040-5760/09/4503-0180

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Section: Resultssupporting

confidence: 81%

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confidence: 99%

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Effect of the target on the efficiency of generation of monomolecular ions of fluorine-containing amino acids in laser desorption/ionization

et al. 2009

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“…In the electrochemical methods, highly reactive carbon nucleophiles are readily generated at cathodes and then react with CO 2 immediately to provide the corresponding carboxylated products. Over the past several decades, there have been many reports on the electrochemical fixation of CO 2 to various types of organic compounds such as organohalides [6][7][8][9][10][11][12][13][14][15][16], activated olefins [17][18][19], imines [20][21][22][23][24], and ketones [25][26][27][28] in conventional polar organic solvents. In addition, some of them focused on the effect of the pressure of CO 2 on electrocarboxylation processes [27,28].…”

Section: Introductionmentioning

confidence: 99%

Electrochemical fixation of CO2 to organohalides in room-temperature ionic liquids under supercritical CO2

Tateno

Nakabayashi

Kashiwagi

et al. 2015

Electrochimica Acta

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“…Under some circumstances, it could easily react with carbanions to produce organic carboxylates (Eq. (5)), [18][19][20][21][22][23] some of which are industrial interest, such as for anti-inflammatory drugs. Hence, much attention has been paid in the electroreduction of organic halides in the presence of CO 2 in the last decades [24][25][26][27].…”

Section: Introductionmentioning

confidence: 99%

Electroreduction of dibromobenzenes on silver electrode in the presence of CO2

Lan

Wang

et al. 2012

Journal of Electroanalytical Chemistry

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Electrochemical carboxylation of fluorocontaining imines with preparation of fluorinated N-phenylphenylglycines

Cited by 46 publications

References 29 publications

Effect of the target on the efficiency of generation of monomolecular ions of fluorine-containing amino acids in laser desorption/ionization

Effect of the target on the efficiency of generation of monomolecular ions of fluorine-containing amino acids in laser desorption/ionization

Electrochemical fixation of CO2 to organohalides in room-temperature ionic liquids under supercritical CO2

Electroreduction of dibromobenzenes on silver electrode in the presence of CO2

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