Acid‐Functionalised Magnetic Ionic Liquid [AcMIm]FeCl<sub>4</sub> as Catalyst for Oxidative Hydroxylation of Arylboronic Acids and Regioselective Friedel–Crafts Acylation

Saha, Arijit; Payra, Soumen; Dutta, Dibyendu; Banerjee, Subhash

doi:10.1002/cplu.201700221

Cited by 27 publications

(16 citation statements)

References 57 publications

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“…The interpretations were achieved considering the literature. [11,12,[50][51][52] Magnetic property of N 1 ,N 1 ,N 2 ,N 2 -tetramethyl-N 1 ,N 2bis(sulfo)ethane-1,2-diaminium tetrachloroferrate was determined by a vibrating sample magnetometer at room temperature; the VSM plot is demonstrated in Figure 7. A linear plot was observed for our catalyst, indicating the paramagnetic property (a paramagnetic material is weakly attracted by an external magnetic field and forms internal induced magnetic fields in the direction of the external applied magnetic field).…”

Section: The Catalyst Characterizationmentioning

confidence: 99%

“…A linear plot was observed for our catalyst, indicating the paramagnetic property (a paramagnetic material is weakly attracted by an external magnetic field and forms internal induced magnetic fields in the direction of the external applied magnetic field). [50,53] were obtained at 80 C using 10 mol% of the catalyst (the reaction time: 10 min; yield: 96%). Increasing the catalyst amount up to 12 mol% and the temperature up to 90 C has no significant effect on the reaction time and yield.…”

Section: The Catalyst Characterizationmentioning

confidence: 99%

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Synthesis and characterization of a novel organic–inorganic hybrid salt and its application as a highly effectual Brønsted–Lewis acidic catalyst for the production of N,N′‐alkylidene bisamides

Zare

Monfared

Sajadikhah

2020

Applied Organom Chemis

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In this research, a novel organic-inorganic hybrid salt, namely, N 1 ,N 1 ,N 2 ,N 2-tetramethyl-N 1 ,N 2-bis(sulfo)ethane-1,2-diaminium tetrachloroferrate ([TMBSED] [FeCl 4 ] 2) was prepared and characterized by Fourier-transform infrared spectroscopy (FT-IR), energy-dispersive X-ray spectroscopy (EDX), elemental mapping, field emission scanning electron microscopy (FE-SEM), X-ray diffraction (XRD), thermal gravimetric (TG), differential thermal gravimetric (DTG), and vibrating-sample magnetometry (VSM) analyses. Catalytic activity of the hybrid salt was tested for the synthesis of N,N 0-alkylidene bisamides through the reaction of benzamide (2 eq.) and aromatic aldehydes (1 eq.) under solvent-free conditions in which the products were obtained in high yields and short reaction times. The catalyst was superior to many of the reported catalysts in terms of two or more of these factors: the reaction medium and temperature, yield, time, and turnover frequency (TOF). [TMBSED][FeCl 4 ] 2 is a Brønsted-Lewis acidic catalyst; there are two SO 3 H groups (as Brønsted acidic sites) and two tetrachloroferrate anions (as Lewis acidic sites) in its structure. Highly effectiveness of the catalyst for the synthesis of N,N 0-alkylidene bisamides can be attributed to synergy of the Brønsted and Lewis acids and also possessing two sites of each acid.

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Section: The Catalyst Characterizationmentioning

confidence: 99%

Section: The Catalyst Characterizationmentioning

confidence: 99%

Synthesis and characterization of a novel organic–inorganic hybrid salt and its application as a highly effectual Brønsted–Lewis acidic catalyst for the production of N,N′‐alkylidene bisamides

Zare

Monfared

Sajadikhah

2020

Applied Organom Chemis

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“…As environmentally benign reaction media and/or catalysts, ionic liquids (ILs) have been used in a wide range of organic syntheses. Recently, Banerjee and our group reported the oxidative hydroxylation of arylboronic acids using acid‐functionalized magnetic IL and the readily available IL, 1‐butyl‐3‐methylimdazoline chloride ([bmim]Cl), respectively. Both approaches gave the desired products in excellent fashion.…”

Section: Optimization Of Amount Of Pcl and H2o2 For Hydroxylation Of mentioning

confidence: 99%

Highly Porous Polycaprolactone Membrane: A Biocompatible Promotor for Oxidative Hydroxylation of Arylboronic Acids

Kwon

Lim

Shin

et al. 2020

Bulletin Korean Chem Soc

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“…Therefore, the research on the development of new MILs and exploration of their properties and applications have fascinated devastating interest in recent times due to limited reports. Previously, we have developed a new task-specific imidazolium-based magnetic acidic ionic liquids, [AcMIm]FeCl 4 (1-acyl-3methylimidazolium tetrachloroferrate) and its application in the oxidative hydroxylation of arylboronic acids leading to functionalized phenols and subsequent acylation of phenols to acylated phenols via C-C bond formations under external acid/base/ligand free conditions [8]. In this paper, we have demonstrated the excellent catalytic activity of [AcMIm]FeCl 4 in one-pot multicomponent reactions for the synthesis of biologically important tetrahydrobenzo[b]pyran derivatives (Scheme 1).…”

Section: Introductionmentioning

confidence: 99%

[AcMIM]FeCl4: A Magnetically Separable Organocatalyst for the Clean Synthesis of Tetrahydrobenzo[b]pyran Derivatives

Saha

Payra

Asatkar

et al. 2019

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Background: Recently, organic synthesis using ionic liquids (ILs) via green approach has attracted considerable attention to address the problem associated with environmental pollution. Magnetization of ILs provides added advantages of separation by external magnet. This can be accomplished by incorporation of high-spin iron(III) in the form of tetrachloro or tetrabromoferrate( III). Thus, synthesis of novel magnetically separable ILs for organic transformations is highly desirable. Results: [AcMIm]FeCl4 ionic liquid showed excellent catalytic activity in the one pot threecomponent synthesis tetrahydrobenzo[b]pyran derivatives at room temperature in excellent yields (94-98 %) within short reaction time (15-20 min.). The ILs were recovered and reused for at least six times with the minimum loss of catalytic activity. Methods: Here, we have demonstrated the excellent catalytic activity of acid functionalized magnetic Ils, [AcMIm]FeCl4 in one-pot multicomponent reactions for the synthesis of biologically important tetrahydrobenzo[b]pyran derivatives. Conclusion: A facile and convenient methodology has been developed for the synthesis of bio-active tetrahydrobenzo[b]pyran derivatives using [AcMIm]FeCl4 ionic liquid as an sufficient and reusable catalyst under environment-benign conditions.

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Acid‐Functionalised Magnetic Ionic Liquid [AcMIm]FeCl₄ as Catalyst for Oxidative Hydroxylation of Arylboronic Acids and Regioselective Friedel–Crafts Acylation

Abstract: Scheme1.Synthesis of at ask-specific,acidic MAIL and its applicationsino rganic transformations.[**] [AcMIm]FeCl 4 = 1-acyl-3-methylimidazolium tetrachloroferrate.Supporting informationfor this article can be found under: https://doi.

Cited by 27 publications

References 57 publications

Synthesis and characterization of a novel organic–inorganic hybrid salt and its application as a highly effectual Brønsted–Lewis acidic catalyst for the production of N,N′‐alkylidene bisamides

Synthesis and characterization of a novel organic–inorganic hybrid salt and its application as a highly effectual Brønsted–Lewis acidic catalyst for the production of N,N′‐alkylidene bisamides

Highly Porous Polycaprolactone Membrane: A Biocompatible Promotor for Oxidative Hydroxylation of Arylboronic Acids

[AcMIM]FeCl4: A Magnetically Separable Organocatalyst for the Clean Synthesis of Tetrahydrobenzo[b]pyran Derivatives

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Acid‐Functionalised Magnetic Ionic Liquid [AcMIm]FeCl4 as Catalyst for Oxidative Hydroxylation of Arylboronic Acids and Regioselective Friedel–Crafts Acylation

Abstract: Scheme1.Synthesis of at ask-specific,acidic MAIL and its applicationsino rganic transformations.[**] [AcMIm]FeCl 4 = 1-acyl-3-methylimidazolium tetrachloroferrate.Supporting informationfor this article can be found under: https://doi.

Cited by 27 publications

References 57 publications

Synthesis and characterization of a novel organic–inorganic hybrid salt and its application as a highly effectual Brønsted–Lewis acidic catalyst for the production of N,N′‐alkylidene bisamides

Synthesis and characterization of a novel organic–inorganic hybrid salt and its application as a highly effectual Brønsted–Lewis acidic catalyst for the production of N,N′‐alkylidene bisamides

Highly Porous Polycaprolactone Membrane: A Biocompatible Promotor for Oxidative Hydroxylation of Arylboronic Acids

[AcMIM]FeCl4: A Magnetically Separable Organocatalyst for the Clean Synthesis of Tetrahydrobenzo[b]pyran Derivatives

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Acid‐Functionalised Magnetic Ionic Liquid [AcMIm]FeCl₄ as Catalyst for Oxidative Hydroxylation of Arylboronic Acids and Regioselective Friedel–Crafts Acylation