Ligand-free Pd(0)/SiO<sub>2</sub>-catalyzed aminocarbonylation of aryl iodides to amides under atmospheric CO pressure

Hu, Qinhua; Wang, Lele; Wang, Chen; Wu, Yao; Ding, Zhengxin; Yuan, Rusheng

doi:10.1039/c7ra04985d

Cited by 13 publications

(4 citation statements)

References 47 publications

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“…It is also indicated that previous results relied on very high pressure (5–20 bar) of CO in the absence of a CO absorbent (Table S4, Supporting Information). 37‐40 Thus, the reactive absorption of CO by [BimH]Cl‐CuCl‐1.0ZnCl 2 can dramatically decrease the pressure and efficiently promote carbonylation reaction to obtain 70–97 yields.…”

Section: Resultsmentioning

confidence: 99%

Promoted absorption of CO at high temperature by cuprous‐based ternary deep eutectic solvents

Tao

et al. 2020

AIChE Journal

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Achieving efficient dissolution of carbon monoxide (CO) in the solvent is very helpful for the implementation of carbonylation reaction at ambient pressure. However, almost all of common solvents show very low solubilities of CO at high temperature. Herein, a series of cuprous‐based ternary deep eutectic solvent (DES) was prepared by mixing imidazolium hydrochloride with CuCl and ZnCl2. The ternary DES [BimH]Cl‐CuCl‐1.0ZnCl2 exhibited very large CO absorption capacity (0.075 mol mol−1, 1 bar) even at a high temperature (353.2 K), which is superior to all of the reported absorbents. Moreover, the ternary DES [BimH]Cl‐CuCl‐1.0ZnCl2 could further promote the reactive absorption of CO to conduct the aminocarbonylation reaction effortlessly at ambient pressure, and thus the targeted products benzamides were obtained in 70–97 yields. We believe that this finding opens a new way to design advanced solvents for efficient capture of CO at high temperature.

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Section: Resultsmentioning

confidence: 99%

Promoted absorption of CO at high temperature by cuprous‐based ternary deep eutectic solvents

Tao

et al. 2020

AIChE Journal

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“…Characterization data for arylsilanes and amides products have been previously reported. ,,, All arylsilanes were compared with literature data: trimethoxy( p -tolyl)silane, trimethoxy(4-methoxyphenyl)silane, (4-fluorophenyl)trimethoxysilane, (4-chlorophenyl)trimethoxysilane, (4-bromophenyl)trimethoxysilane, trimethoxy( m -tolyl)silane, trimethoxy(3-methoxyphenyl)silane, (3-fluorophenyl)trimethoxysilane, (3-chlorophenyl)trimethoxysilane, (3,5-dimethylphenyl)trimethoxysilane, trimethoxy(naphthalen-2-yl)silane…”

Section: Methodsmentioning

confidence: 99%

Synthesis of Amides by Mild Palladium-Catalyzed Aminocarbonylation of Arylsilanes with Amines Enabled by Copper(II) Fluoride

Zhang

Hou

et al. 2018

J. Org. Chem.

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A general Pd-catalyzed synthesis of amides by oxidative aminocarbonylation of arylsilanes under mild conditions was accomplished for the first time. The reaction is promoted by a commercially available copper(II) fluoride, which acts as a dual silane activator and mild oxidant, enabling highly efficient aminocarbonylation of versatile arylsilanes at atmospheric CO pressure. The reaction is tolerant of a wide range of arylsilanes and various sensitive halide functional groups as well as a broad scope of amines are compatible with this oxidative process using cheap CO. A significant aspect involves the increased efficiency by the catalyst system. The reaction represents a segue into the powerful Pd-catalyzed oxidative transformations of organosilanes.

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“…[44d-e] In a related work, ligand free Pd(0)/SiO 2 catalyzed aminocarbonylation in presence of atmospheric CO has been developed by Yuan and co-workers (Scheme 26). [45] The catalyst displayed good recyclability and can be applied for synthesis of diverse array of substituted amides. However, very low yields were obtained when alkyl amines were utilized as amine source.…”

Section: Supported Palladium Catalysts In Aminocarbonylationmentioning

confidence: 99%

Supported Palladium Catalyzed Carbonylative Coupling Reactions using Carbon Monoxide as C1 Source

Shaifali

Sheetal

Das

2021

The Chemical Record

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The carbonylative reactions of aryl halides, boronic acids, amines, activated alkene and alkynes under CO and supported palladium catalyzed conditions are very popular reactions for the synthesis of bioactive molecules, pharmaceuticals, polymers, peptides, intermediates and fine chemicals synthesis. Due to cost effectiveness and easy handling of recyclable supported palladium catalyst, it became more popular among researchers either working in academic institute or industry. In recent years, irrespective of poisoning effect of CO with palladium as major limitation, several advancements have been done through surface selection, designing and condition improvement to achieve high yield in the area of carbonylative coupling reactions. We hope this review will be helpful as a ready reference of last 20 years in the field of CO insertion reactions using diverse range of supported palladium catalysts under carbon monoxide or its sources as C1 source.

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Ligand-free Pd(0)/SiO₂-catalyzed aminocarbonylation of aryl iodides to amides under atmospheric CO pressure

Cited by 13 publications

References 47 publications

Promoted absorption of CO at high temperature by cuprous‐based ternary deep eutectic solvents

Promoted absorption of CO at high temperature by cuprous‐based ternary deep eutectic solvents

Synthesis of Amides by Mild Palladium-Catalyzed Aminocarbonylation of Arylsilanes with Amines Enabled by Copper(II) Fluoride

Supported Palladium Catalyzed Carbonylative Coupling Reactions using Carbon Monoxide as C1 Source

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Ligand-free Pd(0)/SiO2-catalyzed aminocarbonylation of aryl iodides to amides under atmospheric CO pressure

Cited by 13 publications

References 47 publications

Promoted absorption of CO at high temperature by cuprous‐based ternary deep eutectic solvents

Promoted absorption of CO at high temperature by cuprous‐based ternary deep eutectic solvents

Synthesis of Amides by Mild Palladium-Catalyzed Aminocarbonylation of Arylsilanes with Amines Enabled by Copper(II) Fluoride

Supported Palladium Catalyzed Carbonylative Coupling Reactions using Carbon Monoxide as C1 Source

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Ligand-free Pd(0)/SiO₂-catalyzed aminocarbonylation of aryl iodides to amides under atmospheric CO pressure