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A Combination of Biocompatible Room Temperature Ionic Liquid and Supported Palladium Nanoparticles Catalyst for Aminocarbonylation and Alkoxycarbonylation

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Abstract

An efficient and environmentally benign protocol is accomplished for the rapid production of amide and carboxylic ester via aminocarbonylation and alkoxycarbonylation of aryl halides with various amines and alcohols, respectively. The protocol is advantageous compared to those reported in the literature including using a recyclable heterogeneous palladium catalyst comprising palladium nanoparticles immobilized on magnetic covalent triazine-based framework (CTF) support (Pd/Fe3O4@SiO2-CTF), safe Mo(CO)6 as the solid CO source, being environmentally more benign due to using a readily-available and biodegradable room-temperature ionic liquid, choline hydroxide (ChOH), serves a dual role as solvent as well as the base without addition of auxiliary base. More significantly, Pd/Fe3O4@SiO2-CTF showed good recyclability, recycled six times with negligible change in catalytic performance which is an important characteristic from the viewpoint of sustainable chemistry.

Graphical Abstract

An efficient and clean protocol has been developed for the rapid production of amide and carboxylic ester via aminocarbonylation and alkoxycarbonylation of aryl halides with various amines and alcohols, respectively. The protocol is advantageous due to using a recyclable heterogeneous palladium catalyst (Pd/Fe3O4@SiO2@CTF), safe Mo(CO)6 as the solid CO source, and a readily available and biodegradable room-temperature ionic liquid, choline hydroxide (ChOH), dually as solvent and the base to scavenge the acid of hydrogen halide (HX) without addition of auxiliary base. More significantly, Pd/Fe3O4@SiO2@CTF showed good recyclability, recycled six times with negligible change in catalytic performance which is an important characteristic from the viewpoint of sustainable chemistry.

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Acknowledgements

We are grateful to Tarbiat Modares University for financial support of this work.

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  1. Masoumeh Jadidi Nejad and Monire Shariatipour have contributed equally to this work.

Authors and Affiliations

  1. Chemistry Department, Tarbiat Modares University, P.O. Box, Tehran, 14155-4838, Iran

    Masoumeh Jadidi Nejad, Monire Shariatipour & Akbar Heydari

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  1. Masoumeh Jadidi Nejad
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Jadidi Nejad, M., Shariatipour, M. & Heydari, A. A Combination of Biocompatible Room Temperature Ionic Liquid and Supported Palladium Nanoparticles Catalyst for Aminocarbonylation and Alkoxycarbonylation. Catal Lett 153, 1957–1973 (2023). https://doi.org/10.1007/s10562-022-04141-w

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