A novel system for the Suzuki cross-coupling reaction catalysed with light fluorous palladium–NHC complex

Yu, Hong; Wan, Li; Cai, Chun

doi:10.1016/j.jfluchem.2012.08.005

Cited by 11 publications

(5 citation statements)

References 32 publications

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“…Similar catalytic results for the Suzuki-Miyaura cross-coupling reactions have also been obtained using Pd(OAc) 2 or PdCl 2 , base and benzimidazole or imidazole catalytic systems bearing different electron-donating or electron-withdrawing aryl, substituted aryl, alkyl and substituted alkyl groups on benzimidazole or imidazole ligands [51,52,53]. A comparison of our catalytic system consisting of Pd(OAc) 2 /benzimidazolium salt/K 2 CO 3 in DMF/H 2 O under microwave heating with similar catalytic systems including NHC ligand [8,14,54,55,56], under conventional heating clearly indicates that microwave heating improves in catalytic yields and reaction times.…”

Section: Resultsmentioning

confidence: 99%

Synthesis, Characterization and Microwave-Promoted Catalytic Activity of Novel N-phenylbenzimidazolium Salts in Heck-Mizoroki and Suzuki-Miyaura Cross-Coupling Reactions under Mild Conditions

et al. 2013

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A number of novel benzimidazolium salts having aryl substituents such as N-phenyl, 4-chlorophenyl and various alkyl substituents were synthesized. Their microwave-assisted catalytic activities were evaluated in Heck-Mizoroki and Suzuki-Miyaura cross-coupling reactions using a catalytic system consisting of Pd(OAc) 2 /K 2 CO 3 in DMF/H 2 O under mild reaction conditions with consistent high yields, except those of 2-bromopyridine.

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Section: Resultsmentioning

confidence: 99%

Synthesis, Characterization and Microwave-Promoted Catalytic Activity of Novel N-phenylbenzimidazolium Salts in Heck-Mizoroki and Suzuki-Miyaura Cross-Coupling Reactions under Mild Conditions

et al. 2013

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“…To access a perfluoroalkylated imidazolium derivative, we first tried to dialkylate imidazole 8 with triflate 7 , derived from the alcohol n F 13 C 6 CH 2 CH 2 OH according to a known procedure, but our attempts were unsuccessful. We then turned to 1‐trimethylsilylimidazole ( 6 ), which was reported to give superior results in alkylation reactions, and we were indeed able to isolate the triflate salt 3e in 35 % yield after recrystallization (Scheme ).…”

Section: Resultsmentioning

confidence: 99%

“…Whereas the pyridinium scaffold has so far not been equipped with fluorinated residues, the imidazolium core has been targeted for the development of new fluorinated N‐heterocyclic carbene ligands for homogeneous catalysis . Herein, we wish to disclose the synthesis of a small series of 30 fluorinated ionic liquids based on the two pyridinium cations 1 and 2 as well as the imidazolium cation 3 (Figure ). To access a divers set of compounds for screening the material properties, we have focused on the exchange of anions …”

Section: Introductionmentioning

confidence: 99%

Perfluorinated Pyridinium and Imidazolium Ionic Liquids

Alpers

Schmidtmann

Muesmann³

et al. 2017

Eur J Org Chem

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Ionic liquids with perfluorinated side chains were prepared as hybrid materials for surface impregnation. For the cationic part, methyl and ethyl pyridinium as well as imidazolium scaffolds were used. The anions investigated were hydroxide, acetate, trifluoroacetate, triflate, triflimide, chloride, bromide, iodide, hydrogensulfate, and perfluorododecanoate. A key feature of this investigation is the finding that the use of relatively short perfluorohexyl residues as the fluorinated part of the salts is beneficial for the target compounds compared with established products, because of their lower bioaccumulativity. One compound yielded single crystals that were suitable for X‐ray structure analysis, revealing a layered structure with relatively well‐resolved, hard ionic domains alternating with disordered, soft perfluorinated layers. The wettability of all 30 materials was investigated by water contact angle measurements of a thin film on a glass surface. In two cases, promising contact angles (130° and 140°) were observed, indicating that the products might be suitable candidates for the impregnation of surfaces.

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“…In general, from the very onset of academic and industrial research on NHC complexes, studies of perfluoroalkyl-or perfluoralkylene containing NHC derivatives have been communicated regularly, but only sparsely with regard to this special area [34][35][36][37][38][39][40][41][42][43][44][45][46].…”

Section: Introductionmentioning

confidence: 99%

A Fluoroponytailed NHC–Silver Complex Formed from Vinylimidazolium/AgNO3 under Aqueous–Ammoniacal Conditions

et al. 2022

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3-(1H,1H,2H,2H-Perfluorooctyl)-1-vinylimidazolium chloride [2126844–17–3], a strong fluorosurfactant with remarkably high solubility in water, was expediently converted into the respective doubly NHC-complexed silver salt with nitrate as counter ion in quantitative yield. Due to its vinyl substituents, [bis(3-(1H,1H,2H,2H-perfluorooctyl)-1-vinylimidazol-2-ylidene)silver(I)] nitrate, Ag(FNHC)2NO3, represents a polymerizable N-heterocyclic carbene transfer reagent, thus potentially offering simple and robust access to coordination polymers with crosslinking metal bridges. The compound was characterized by infrared and NMR spectroscopy, mass spectrometry as well as elemental analysis, and supplemented by X-ray single-crystal structure determination. It crystallizes in the monoclinic crystal system in the space group P21/c. With 173.3°, the geometry of the Ag-carbene bridge deviates slightly from linearity. The disordered perfluoroalkyl side chains exhibit a helical conformation.

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A novel system for the Suzuki cross-coupling reaction catalysed with light fluorous palladium–NHC complex

Cited by 11 publications

References 32 publications

Synthesis, Characterization and Microwave-Promoted Catalytic Activity of Novel N-phenylbenzimidazolium Salts in Heck-Mizoroki and Suzuki-Miyaura Cross-Coupling Reactions under Mild Conditions

Synthesis, Characterization and Microwave-Promoted Catalytic Activity of Novel N-phenylbenzimidazolium Salts in Heck-Mizoroki and Suzuki-Miyaura Cross-Coupling Reactions under Mild Conditions

Perfluorinated Pyridinium and Imidazolium Ionic Liquids

A Fluoroponytailed NHC–Silver Complex Formed from Vinylimidazolium/AgNO3 under Aqueous–Ammoniacal Conditions

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