Basic Ionic Liquid as Catalysis and Reaction Medium:  A Novel and Green Protocol for the Markovnikov Addition of <i>N</i>-Heterocycles to Vinyl Esters, Using a Task-Specific Ionic Liquid, [bmIm]OH

Xu, Jia‐Zhuang; Liu, Bo‐Kai; Wu, Wen; Qian, Chao; Wu, Qi; Lin, Xianfu

doi:10.1021/jo0600914

Cited by 124 publications

(48 citation statements)

References 29 publications

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“…Various schemes were employed to separate the nucleophile from the metal cation, but even strong bases such as the crown ether are not very good for that purpose. Ionic liquids and molten salts [16][17][18][19][20][21][22][23][24] have recently been found to be quite useful for some organic reactions. For example, D'Anna and co-workers found that in S N Ar reactions amines react faster in ionic liquids than in molecular solvents by almost 1 or 3 orders of magnitude.…”

Section: -15mentioning

confidence: 99%

“…There are also situations in which the S N Ar reactions are much more advantageous. For example, the S N Ar procedure is known to be far more selective than electrophilic substitution for producing highly specific 18 F compounds to be used as noninvasive imaging agents to study and probe the molecular and biological processes in living systems with positron emission tomography (PET).…”

Section: Introductionmentioning

confidence: 99%

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Very Efficient Nucleophilic Aromatic Fluorination Reaction in Molten Salts: A Mechanistic Study

Jang¹,

Park²,

Lee³

et al. 2012

Bulletin of the Korean Chemical Society

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We report a quantum chemical study of an extremely efficient nucleophilic aromatic fluorination in molten salts. We describe that the mechanism involves solvent anion interacting with the ion pair nucleophile M + F − (M = Na, K, Rb, Cs) to accelerate the reaction. We show that our proposed mechanism may well explain the excellent efficiency of molten salts for S N Ar reactions, the relative efficacy of the metal cations, and also the observed large difference in rate constants in two molten salts (n-C 4 H 9 ) 4 N + CX 3 SO 3 − , (X=H, F) with slightly different sidechain (-CH 3 vs. -CF 3 ).

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Section: -15mentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Very Efficient Nucleophilic Aromatic Fluorination Reaction in Molten Salts: A Mechanistic Study

Jang¹,

Park²,

Lee³

et al. 2012

Bulletin of the Korean Chemical Society

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“…However, the ability of an ionic liquid as a clean catalyst and reagent has not been explored to any great extent although it is of much importance in the context of the green synthesis [13,14].…”

Section: Introductionmentioning

confidence: 99%

Basic GO-Imidazolium ionic liquid as a recoverable nanocatalyst for the synthesis of pyrrole derivatives

Zand

Ghafuri

2017

Proceedings of the 21st International Electronic Conference on Synthetic Organic Chemistry

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Ionic liquid with basic properties is a significant category in the wide-ranging ionic liquid field.Ionic liquids are mostly made of ions and ion pairs. They are known as powerful solvents which have potential applications. Since the 1999 review by Welton which is about room temperature ionic liquids, ionic liquids have grown as a motivating research area in the last 15 years. Some ionic liquids are liquid at room temperature include some nitrogen-based compounds. Among them, imidazolium-based ionic liquids are the most important ones. In imidazole-based ionic liquids, their physical properties like melting point and acidity-basicity could be adjusted by changing the alkyl substituents and ion pairs. Most of room temperature ionic liquids involve bulky organic cations such as 1-alkyl-3-methylimidazolium, 1-alkylpyridinium and ammonium ion. To have heterogeneous nanocatalysts using ionic liquids, it was studied that carbonaceous substrates with high surface area like graphene oxide could be the best choice.To this purpose and to have heterogeneous basic nanocatalyst with high surface area and significant catalytic activity, basic GO-Imidazolium ionic liquid was synthesized in this research.Here, N-methyl imidazole was used as cation, HCO3-as anion and GO as solid support to form basic ionic liquid nanocatalyst and its catalytic ability was used in synthesis of pyrroles as a significant N-heterocycle compound with important biological and pharmacological activity.

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“…3-Benzyl substituted 4-hydroxycoumarin derivatives are components of numerous natural products like warfarin, phenprocoumon, coumatetralyl, carbochromen, bromadialone, etc. These compounds also exhibit a wide band of biological activities including antibacterial, anti-HIV [7], antiviral [8], anticoagulant [9], antioxidant [10] and anticancer activities [11]. The vast biological significance of the amino derivatives of 4-hydroxycoumarin inspired us to develop a novel protocol for the efficient synthesis of new benzylamine coumarin derivatives.…”

Section: Introductionmentioning

confidence: 99%

PEG Mediated Eco-Friendly One Pot Sunthesis of Benzylamine Coumarin Derivatives Using Multicomponent Reactant

Viradiya

Kotadiya

Khunt

et al. 2014

ILCPA

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A green resourceful, eco-friendly and facile protocol was developed for the synthesis of benzylamine coumarin derivatives by the reaction of 4-hydroxy coumarin, secondary amine and aromatic aldehyde in the presence of PEG 400 as a solvent as well as catalyst at room temperature. A wide range of functional groups were tolerated in the developed protocol. The structures of all the synthesized compounds were confirmed by 1 H NMR, IR, MASS and Elemental Analysis. The target molecules were obtained in good to excellent yield applying this method.

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Basic Ionic Liquid as Catalysis and Reaction Medium: A Novel and Green Protocol for the Markovnikov Addition of N-Heterocycles to Vinyl Esters, Using a Task-Specific Ionic Liquid, [bmIm]OH

Cited by 124 publications

References 29 publications

Very Efficient Nucleophilic Aromatic Fluorination Reaction in Molten Salts: A Mechanistic Study

Very Efficient Nucleophilic Aromatic Fluorination Reaction in Molten Salts: A Mechanistic Study

Basic GO-Imidazolium ionic liquid as a recoverable nanocatalyst for the synthesis of pyrrole derivatives

PEG Mediated Eco-Friendly One Pot Sunthesis of Benzylamine Coumarin Derivatives Using Multicomponent Reactant

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