Synthetic and structural studies on pentafluorobenzylated imidazole systems

Lampl, Martin; Schlapp‐Hackl, Inge; Wurst, Klaus; Gelbrich, Thomas; Kopacka, Holger; Müller, Thomas; Kreutz, Christoph; Naier, Benjamin; Partl, Gabriel; Kahlenberg, Volker; Amer, Hassan; Bacher, Markus; Rosenau, Thomas; Huppertz, Hubert; Schottenberger, Herwig

doi:10.1016/j.jfluchem.2018.11.019

Cited by 4 publications

(7 citation statements)

References 55 publications

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“…Taking advantage of this result and inspired by a previous report of Lamp et al, we attempted to use 1 as a key intermediate to prepare a toolbox of active ILs (2-7). [19] Substituents include benzyl, para-substituted methyl benzoate, para-substituted benzoic acids, coumarin, butanoate and polyethylene glycol 2 (PEG2). All active ILs were synthesized with isolated yields ranging from 89-100 % following liquid-liquid extraction and freeze-drying (Figure 2b).…”

Section: Resultsmentioning

confidence: 99%

“…The synthesis of thione 1 under inert conditions was monitored over time using high‐performance liquid chromatography (HPLC) as illustrated in Figure S1. Taking advantage of this result and inspired by a previous report of Lamp et al., we attempted to use 1 as a key intermediate to prepare a toolbox of active ILs ( 2 – 7 ) [19] . Substituents include benzyl, para ‐substituted methyl benzoate, para ‐substituted benzoic acids, coumarin, butanoate and polyethylene glycol 2 (PEG2).…”

Section: Resultsmentioning

confidence: 99%

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Ionic Liquid‐Mediated Approach for the Synthesis of Site‐Specific Thioether Conjugates

Abujubara

Yang

Otyakmaz

et al. 2023

Chemistry A European J

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Site-specific conjugation approaches are of great importance in drug discovery, notably for the synthesis of biochemical probes or molecular conjugates for targeted delivery. Herein, we report a mild ionic liquid (IL)-mediated thiolation technique that relies on the use of 1,3-ethyl-methyl imidazolium acetate, [C 2 mim][OAc] as a solvent and precursor to generate activated IL, as well as a solvent for the conjugation reaction. First, a focused library of active ILs was prepared for functionalizing/conjugating cysteine-containing small molecules and unprotected peptides. Interestingly, a bifunctional active IL could also be successfully employed as a linker for the conjugation of peptides lacking Cys. This study sets the ground for further investigation of the use of active ILs for modifying, labeling or conjugating larger and more complex therapeutic modalities such as proteins and antibodies.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Ionic Liquid‐Mediated Approach for the Synthesis of Site‐Specific Thioether Conjugates

Abujubara

Yang

Otyakmaz

et al. 2023

Chemistry A European J

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“…The title compound (2) was synthesized in two steps from 1,3-bis(2,3,4,5,6pentafluorobenzyl)imidazolium bromide [14]. Treatment of this salt with silver oxide afforded the silver carbene complex [AgBr{κC-1,3-(C 6 F 5 CH 2 ) 2 N 2 C 3 H 2 }], which was added to (η 5 -pentamethylcyclopentadienyl)iridium dichloride dimer (Scheme 1).…”

Section: Resultsmentioning

confidence: 99%

(η5-Pentamethylcyclopentadienyl)iridium{1,3-bis(2,3,4,5,6-pentafluorobenzyl)imidazolin-2-ylidene}dichloride

Bandaru

Marr

Saunders

2023

Molbank

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In this paper, we report (η5-pentamethylcyclopentadienyl)iridium{1,3-bis(2,3,4,5,6-pentafluorobenzyl)imidazolin-2-ylidene}dichloride, 2, synthesized using a silver transfer agent generated from 1,3-bis(2,3,4,5,6-pentafluorobenzyl)imidazolium bromide. Compound 2 was characterized using 1H and 19F NMR spectroscopy and mass spectrometry, and its structure was determined in a single-crystal X-ray diffraction study.

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“…The majority of crystal structures of fluoroaryl-substituted imidazolium bromide salts possess a N 2 C─HꞏꞏꞏBrhydrogen bond [2,3,[9][10][11], unless this position is blocked, as is the case for 2-methyl substituted imidazolium cations [12]. Typically this charge-assisted hydrogen bonding is the strongest inter-ion interaction [3,8,[11][12][13].…”

Section: Introductionmentioning

confidence: 99%

“…For structures of hydrates there may also be C─HꞏꞏꞏO hydrogen bonding [3,11,14]. In a number of structures the interactions are augmented by anion-π interactions, as occurs for 1-pentafluorophenylmethylimidazolium bromides [7,10].…”

Section: Introductionmentioning

confidence: 99%

The crystal structures of 1-(polyfluorophenylmethyl)-3-methylimidazolium bromide salts

Marr

Saunders

Thomas

2020

Journal of Fluorine Chemistry

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The crystal structures of 1-(2,3,5,6-tetrafluorophenylmethyl)-3-methylimidazolium bromide (2), 1-(2,3,4,5-tetrafluorophenylmethyl)-3-methylimidazolium bromide (3), 1-(2,4,6trifluorophenylmethyl)-3-methylimidazolium bromide (4) and 1-(2,3,6-trifluorophenylmethyl)-3-methylimidazolium bromide ( 5) have been determined. The structures contain non-covalent interactions: hydrogen bonding, anion-π and π-π stacking interactions. The strengths of these interactions have been calculated using DFT. The structures and interactions are compared with those of 1-(2,3,4,5,6-pentafluorophenylmethyl)-3-methylimidazolium bromide (1) and 1-(2,6difluorophenylmethyl)-3-methylimidazolium bromide (6).

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Synthetic and structural studies on pentafluorobenzylated imidazole systems

Cited by 4 publications

References 55 publications

Ionic Liquid‐Mediated Approach for the Synthesis of Site‐Specific Thioether Conjugates

Ionic Liquid‐Mediated Approach for the Synthesis of Site‐Specific Thioether Conjugates

(η5-Pentamethylcyclopentadienyl)iridium{1,3-bis(2,3,4,5,6-pentafluorobenzyl)imidazolin-2-ylidene}dichloride

The crystal structures of 1-(polyfluorophenylmethyl)-3-methylimidazolium bromide salts

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