Facile and efficient Suzuki–Miyaura coupling reaction of aryl halides catalyzed by Pd2(dba)3 in ionic liquid/supercritical carbon dioxide biphasic system

Wang, Hong Bo; Hu, Yinchang; Li, Dejiang

doi:10.1016/j.molliq.2016.02.056

Cited by 30 publications

(4 citation statements)

References 40 publications

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“…Nowadays, RTIL has been widely applied in the field of pharmaceutical separation, electrochemistry, and organic catalysis . To date, various classes of ILs have been employed in the Suzuki reaction, Heck reaction, and Cross-coupling reaction etc. − They often replace hazardous organic solvents and serve as a nonvolatile, environmentally friendly, as well as recyclable catalysts or solvents. Moreover, in the high-temperature- or high-pressure-needed synthetic processes they can be much safer compared with conventional organic solvents, and pressure equipment is no longer needed.…”

Section: Introductionmentioning

confidence: 99%

Temperature-Controlled Mono- and Diolefination of Arene Using Rh(III)/RTIL as an Efficient and Recyclable Catalytic System

Yao

2019

ACS Sustainable Chem. Eng.

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In this report, nonvolatile and chemically stable room-temperature ionic liquid [BMIM]NTf2 was first developed as an excellent reaction medium in the Rh(III)-catalyzed C–H bond-activated olefination. This reaction system is free of any organic solvents and is much safer without the need of pressure-tight equipment. Selective mono- and diolefination has been realized through temperature control for the first time. Room temperature gives mono-olefinated products predominantly with satisfactory yields, while 80 °C selectively generates a high yield of diolefinated products. A wide range of substrate scope with fine yields and satisfactory selectivity is achieved. The reaction can be scaled up to gram scale. Moreover, this catalytic system can be recycled at least 7 times with consistently high catalytic activity. This property reduces environmental contamination caused by the transition metal and saves costs significantly. This reaction approach can be applied in the synthesis of various valuable unsaturated aromatic compounds in academia and industry.

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Section: Introductionmentioning

confidence: 99%

Temperature-Controlled Mono- and Diolefination of Arene Using Rh(III)/RTIL as an Efficient and Recyclable Catalytic System

Yao

2019

ACS Sustainable Chem. Eng.

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“…In the case of catalysis, it can be used like a solid heterogeneous catalyst for continuous fixed-bed reactor systems. , Recently, SILPs have been applied to different catalytic reactions. An efficient catalytic system based on the metal ligand free in an environmental friendly IL system was successfully developed for Suzuki cross-coupling reactions . Another metal/IL supported on nanosilica-based catalysts was employed in the aldehyde C–H activation showing excellent yields of the desired aryl ketones .…”

Section: Introductionmentioning

confidence: 99%

“…An efficient catalytic system based on the metal ligand free in an environmental friendly IL system was successfully developed for Suzuki cross-coupling reactions. 39 Another metal/IL supported on nanosilica-based catalysts was employed in the aldehyde C−H activation showing excellent yields of the desired aryl ketones. 40 Catalysts based on copper-doped silica supporting acidic ILs (based on the [HSO 4 ] − anion) demonstrated a good performance on the Biginelli reaction.…”

Section: ■ Introductionmentioning

confidence: 99%

Methanol-Promoted Oxidation of Nitrogen Oxide (NO_x) by Encapsulated Ionic Liquids

Santiago

Mossin

Bedia

et al. 2019

Environ. Sci. Technol.

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The removal of nitrogen oxides (NO x) has been extensively studied due to their harmful effects to health and environment. In this work, Encapsulated Ionic Liquids (ENILs) are used as catalysts for the NO oxidation at humid conditions and low temperatures. Hollow carbon capsules (C Cap) were first synthetized to contain different amounts of 1-butyl-3-methylimidazolium nitrate IL ([bmim][NO 3 ]), responsible for the catalytic oxidation. Then, the materials were characterized using different techniques, by analyzing microstructure, porosity, elemental composition and thermal stability. The catalytic performance of ENIL materials was tested for NO conversion at different conditions. Thus, NO concentration was fixed at 2,000 ppm at dry and humid conditions. Then, the methanol promotion of the reaction was demonstrated, increasing the NO conversion values in all cases, and the alcohol/water ratio was optimized. The temperature effect was studied as well, using the optimal conditions based on the previous measurements. The results reflect that humid conditions do not have a negative effect in terms of NO conversion when using ENILs, opposite behavior as the observed for C Cap and traditional catalysts studied before. Low amount of IL inside the material (40% in mass) was found to be the optimum for the task, reaching conversions of almost 45% in near industrial conditions of temperature and O 2 and H 2 O concentrations in the flue gas with a GHSV = 10,000 h-1 .

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“…Given these properties, ionic liquids have been widely proposed as solvents for organic reactions at high temperature, for thermal energy storage (TES), as heat-transfer fluids (HTFs), , as high-temperature lubricants, as propellants, and in analytical apparatus. In recent years, ILs have also been successfully used in chemical synthesis, such as for cross-coupling reactions. − Therefore, ILs may be an ideal medium of metal-mediated C–H activation reactions without organic solvents and pressure-tight equipment.…”

Section: Introductionmentioning

confidence: 99%

Imidazolium-Based Ionic Liquid: An Efficient, Normalized, and Recyclable Platform for Rh(III)-Catalyzed Directed C–H Carbenoid Coupling Reactions

Zhang

Chen

Luo

et al. 2018

ACS Sustainable Chem. Eng.

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The ionic liquid [BMIM][NTf2] was developed as an ideal medium in which Rh(III)-catalyzed directed C–H carbenoid coupling reactions can be conducted efficiently and sustainably. More significantly, the ionic liquid can not only achieve the recycle of catalyst system but also improve the efficiency of catalyst, presenting that carbenoid coupling reactions can be accomplished at room temperature within a short period of time. Thus, this work would be useful in expanding applications of C–H activation strategies as tools for assembling novel organic molecules.

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Facile and efficient Suzuki–Miyaura coupling reaction of aryl halides catalyzed by Pd2(dba)3 in ionic liquid/supercritical carbon dioxide biphasic system

Cited by 30 publications

References 40 publications

Temperature-Controlled Mono- and Diolefination of Arene Using Rh(III)/RTIL as an Efficient and Recyclable Catalytic System

Temperature-Controlled Mono- and Diolefination of Arene Using Rh(III)/RTIL as an Efficient and Recyclable Catalytic System

Methanol-Promoted Oxidation of Nitrogen Oxide (NO_x) by Encapsulated Ionic Liquids

Imidazolium-Based Ionic Liquid: An Efficient, Normalized, and Recyclable Platform for Rh(III)-Catalyzed Directed C–H Carbenoid Coupling Reactions

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Facile and efficient Suzuki–Miyaura coupling reaction of aryl halides catalyzed by Pd2(dba)3 in ionic liquid/supercritical carbon dioxide biphasic system

Cited by 30 publications

References 40 publications

Temperature-Controlled Mono- and Diolefination of Arene Using Rh(III)/RTIL as an Efficient and Recyclable Catalytic System

Temperature-Controlled Mono- and Diolefination of Arene Using Rh(III)/RTIL as an Efficient and Recyclable Catalytic System

Methanol-Promoted Oxidation of Nitrogen Oxide (NOx) by Encapsulated Ionic Liquids

Imidazolium-Based Ionic Liquid: An Efficient, Normalized, and Recyclable Platform for Rh(III)-Catalyzed Directed C–H Carbenoid Coupling Reactions

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Methanol-Promoted Oxidation of Nitrogen Oxide (NO_x) by Encapsulated Ionic Liquids