Palladium nanoparticles on a pyridinium supported ionic liquid phase: a recyclable and low-leaching palladium catalyst for aminocarbonylation reactions

Adamcsik, Bernadett; Nagy, Enikő; Urbán, Béla; Szabó, Péter; Pekker, Péter; Skoda‐Földes, Rita

doi:10.1039/d0ra03406a

Cited by 18 publications

(13 citation statements)

References 60 publications

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“…Characterization of the catalyst with 13 C CP MAS NMR, FT-IR and TEM measurements had been reported before. 31 (31) The latter proved the formation of palladium nanoparticles in the diameter range of 1-2 nm that showed more uniform distribution than heterogeneous catalysts obtained from SILPs decorated with imidazolium 33 or phosphonium 34 ions.…”

Section: Scheme 1 Preparation Of the Catalystmentioning

confidence: 96%

“…The catalyst was filtered, dried and was used without further pretreatment. 31 (31) The palladium content of the catalyst was determined by ICP-AES and proved to be in the range of 0.70-0.72% reproducibly. Characterization of the catalyst with 13 C CP MAS NMR, FT-IR and TEM measurements had been reported before.…”

Section: Scheme 1 Preparation Of the Catalystmentioning

confidence: 99%

“…The heterogeneous palladium catalyst was prepared as described before. 31 The synthesis of 3-iodo-2-phenylbenzofuran ( 1) is based on previous publications. 20,35 Since several improvements as well as full characterization of the compounds were carried out, a detailed description is given below.…”

Section: Template For Synthesis Thiemementioning

confidence: 99%

“…In our group, it was shown that a better stabilization of palladium particles could be achieved by a supported pyridinium ionic liquid than using other supported ionic liquid phases (SILPs). 31 The Pd-pyridinium-SILP was proved to be a recyclable and low leaching heterogeneous catalyst in aminocarbonylation reactions of simple model compounds; moreover, it could also be used efficiently in the synthesis of carboxamides with pharmacological importance. In the present study, the main goal was to test the applicability of this palladium catalyst in Suzuki and Sonogashira reactions to convert 3-iodo-2-phenylbenzofuran into a series of 3-aryl- and 3-alkynyl derivatives.…”

Section: Table 1 Screening Of Different Conditions In S...mentioning

confidence: 99%

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Synthesis of 3-Aryl- and 3-Alkynylbenzofurans in the Presence of a Supported Palladium Catalyst

et al. 2022

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Suzuki and Sonogashira coupling reactions of 3-iodo-2-phenylbenzofuran, leading to the corresponding 3-aryl- and 3-alkynyl derivatives, respectively, were carried out using a silica supported pyridinium ionic liquid based heterogeneous catalyst. Under optimized reactions conditions, arylboronic acids with either electron withdrawing or -donating substituents as well as terminal alkynes with aromatic or aliphatic groups could be coupled to the benzofuran skeleton efficiently. The application of this catalyst made it possible to carry out the reaction under phosphine-free and, in case of the Sonogashira coupling, under copper-free conditions. The catalyst retained its activity in at least 7 subsequent runs in both types of reactions. Palladium leaching of less than 1% of the original amount used in the catalytic reaction was observed under optimized conditions in most cases. The methodology was applied successfully in the synthesis of nine different 3-aryl- and ten different 3-alkynyl benzofuran derivatives in moderate to high yields.

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Section: Scheme 1 Preparation Of the Catalystmentioning

confidence: 96%

Section: Scheme 1 Preparation Of the Catalystmentioning

confidence: 99%

Section: Template For Synthesis Thiemementioning

confidence: 99%

Section: Table 1 Screening Of Different Conditions In S...mentioning

confidence: 99%

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Synthesis of 3-Aryl- and 3-Alkynylbenzofurans in the Presence of a Supported Palladium Catalyst

et al. 2022

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“…The latter reaction proved that apart from aryl iodides, iodoalkenes can also be converted into the products with the help of the heterogeneous catalyst. The palladium loss was observed to depend considerably on the nature of the reaction partners [110].…”

Section: Carbonylation Reactions In Ionic Liquid and On Supported Ion...mentioning

confidence: 99%

27 Years of Catalytic Carbonylative Coupling Reactions in Hungary (1994–2021)

2022

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Palladium-catalyzed carbonylation reactions, in the presence of nucleophiles, serve as very potent tools for the conversion of aryl and alkenyl halides or halide equivalents to carboxylic acid derivatives or to other carbonyl compounds. There are a vast number of applications for the synthesis of simple building blocks as well as for the functionalization of biologically important skeletons. This review covers the history of carbonylative coupling reactions in Hungary between the years 1994 and 2021.

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Copper‐Catalyzed Oxidative Amidation for the Synthesis of α‐Ketoamides from α‐Diazoketones with Amines Using Oxygen as Oxidant

et al. 2022

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A novel and efficient CuI‐catalyzed oxidative amidation for the synthesis of α‐ketoamides from α‐diazoketones with amines has been developed, which employs O2 as an environmentally friendly oxidant. Based on control experiments and the reactivity of α‐diazoketones, 2‐morpholino‐1‐phenylethanone was identified as a significant intermediate in this process and a plausible reaction mechanism was proposed. This methodology is a feasible, mild approach to α‐ketoamides in moderate to good yields.

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Palladium nanoparticles on a pyridinium supported ionic liquid phase: a recyclable and low-leaching palladium catalyst for aminocarbonylation reactions

Abstract: SILP catalyst with grafted pyridinium ions was used for either mono- or double carbonylation depending on the reaction conditions. Good recyclability and low palladium loss were observed during the synthesis of pharmaceutically active compounds.

Cited by 18 publications

References 60 publications

Synthesis of 3-Aryl- and 3-Alkynylbenzofurans in the Presence of a Supported Palladium Catalyst

Synthesis of 3-Aryl- and 3-Alkynylbenzofurans in the Presence of a Supported Palladium Catalyst

27 Years of Catalytic Carbonylative Coupling Reactions in Hungary (1994–2021)

Copper‐Catalyzed Oxidative Amidation for the Synthesis of α‐Ketoamides from α‐Diazoketones with Amines Using Oxygen as Oxidant

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