A More Efficient Catalyst for the Carbonylation of Chloroarenes

An efficient system for the direct catalytic intermolecular α-arylation of acetamide derivatives with aryl bromides and chlorides is presented. The palladium catalyst is supported by Kwong’s indole-based phosphine ligand and provides monoarylated amides in up to 95% yield. Excellent chemoselectivities (>10:1) in the mono- and diarylation with aryl bromides were achieved by careful selection of bases, solvents, and stoichiometry. Under the coupling conditions, the weakly acidic α-protons of amides (pKa up to 35) were reversibly depotonated by LiOtBu, NaOtBu, or NaN(SiMe3)2.

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“…33 Palladium catalysts ligated with bidentate ligands activate C–Cl bond, but at temperatures around 100 °C. 34 …”

Section: Resultsmentioning

confidence: 99%

A General and Practical Palladium‐Catalyzed Direct α‐Arylation of Amides with Aryl Halides

2014

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“…The sp 2 CX ( X = Cl, Br, and I) bond in aryl halide greatly affects its Sonogashira reactivity due to the different dissociation energy for splitting the sp 2 CX bond (CCl > CBr > CI) . The Sonogashira‐type CC coupling of aryl iodides with phenylacetylene usually can process well .…”

Section: Synthesis Of Carbon–carbon Bond Compoundsmentioning

confidence: 99%

Metal–Organic Framework Supported Palladium Nanoparticles: Applications and Mechanisms

Yang

Yao

Zhong

et al. 2019

Part & Part Syst Charact

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Heterogeneous palladium (Pd)‐based catalysts are extensively applied to improve the catalytic performance and/or expand the reaction scope in many catalytic processes, involving the cross‐coupling, hydrogenation, reduction, and oxidation reactions. Among them, metal–organic framework (MOF)‐supported Pd nanoparticles (Pd NPs) are becoming the most popular one for their excellent catalytic performance and reusable property. To motivate the development of this technology, the applications of MOF‐supported Pd NPs (Pd NPs/MOFs) in heterogeneous catalysis are critically summarized herein, including the hydrogenation reduction of nitro‐ and polyunsaturated compounds, synthesis of carbon–carbon (CC) bonds compounds, chromium (Cr(VI)) reduction, dehalogenation, alcohol oxidation, CO2 conversion, and CO oxidation. The influences of base, solvents, electron character of substitutes, and type of halogen on the catalytic performance are comprehensively discussed. Finally, the application prospects of Pd NPs/MOFs and existing shortcomings in the catalytic field are proposed.

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“…Molecular oxygen [45,46], 1-propyne [47], and ethene [48,49] have also seen use as reagents in reactions using MW heating. Palladium-catalyzed carbonylation chemistry using CO has also been employed extensively in MW vessels [43,44,[50][51][52][53]. Using aryl halides as starting materials, carboxylic acids and esters can be prepared.…”

Section: Use Of Batch Mw Heating For Alkoxycarbonylation Reactionsmentioning

confidence: 99%

Development of methodologies for reactions involving gases as reagents: microwave heating and conventionally-heated continuous-flow processing as examples

Mercadante

Leadbeater

2012

Green Processing and Synthesis

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Microwave (MW) heating and conventionallyheated continuous-flow processing have emerged as viable alternatives to the traditional methods of preparing organic compounds. These tools enable the chemist to circumvent some of the issues associated with conventional processing, while improving the efficiency of chemical transformations. Recently, several strategies have been developed to perform reactions using gaseous reagents, employing MW heating or conventionally-heated microand meso-flow technologies. This perspective describes some of these strategies by means of a discussion of work performed in our laboratory, focused around alkoxycarbonylation and hydrogenation reactions.

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A More Efficient Catalyst for the Carbonylation of Chloroarenes

Cited by 156 publications

References 46 publications

A General and Practical Palladium‐Catalyzed Direct α‐Arylation of Amides with Aryl Halides

A General and Practical Palladium‐Catalyzed Direct α‐Arylation of Amides with Aryl Halides

Metal–Organic Framework Supported Palladium Nanoparticles: Applications and Mechanisms

Development of methodologies for reactions involving gases as reagents: microwave heating and conventionally-heated continuous-flow processing as examples

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