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Proof of Concept: Interface of Recyclable Organogels with Embedded Palladium Nanoparticles Catalyzing Suzuki–Miyaura Coupling in Water at Room Temperature

[Image: see text] A sustainable approach for C–C cross-coupling reaction at room temperature in water has been developed to avoid tedious Pd separation, reduce the carbon footprint, and save energy. Another important aspect is the catalyst recycling and easy product separation. α,γ-Hybrid peptides w...

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Autores principales: Roy Chowdhury, Srayoshi, Nandi, Sujay Kumar, Haldar, Debasish
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2022
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9244900/
https://www.ncbi.nlm.nih.gov/pubmed/35785310
http://dx.doi.org/10.1021/acsomega.2c01360
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author Roy Chowdhury, Srayoshi
Nandi, Sujay Kumar
Haldar, Debasish
author_facet Roy Chowdhury, Srayoshi
Nandi, Sujay Kumar
Haldar, Debasish
author_sort Roy Chowdhury, Srayoshi
collection PubMed
description [Image: see text] A sustainable approach for C–C cross-coupling reaction at room temperature in water has been developed to avoid tedious Pd separation, reduce the carbon footprint, and save energy. Another important aspect is the catalyst recycling and easy product separation. α,γ-Hybrid peptides were designed to selectively use as a ligand for C–C cross-coupling catalysts as well as to form organogels. The peptides form antiparallel sheet-like structures in the solid state. The peptide containing m-aminobenzoic acid, glycine, and dimethylamine forms a whitish gel in toluene, and co-gelation with Pd(OAc)(2) results in light brown gel, which acts as a biphasic catalyst for Suzuki–Miyaura cross-coupling at room temperature in water by mild shaking. The organic–inorganic hybrid gel was characterized by rheology, field-emission scanning electron microscopy, transmission electron microscopy, and energy-dispersive X-ray analyses. On completion of the cross-coupling reaction, the basic aqueous layer (containing products) above the gel can be simply decanted and the intact organic–inorganic hybrid gel can be recycled by topping-up fresh reactants multiple times. The reaction permitted a range of different substitution patterns for aryl and heterocyclic halides with acid or phenol functional groups. Both electron-donating- and electron-withdrawing-substituted substrates exhibited good results for this transformation. The findings inspire toward a holistic green technology for Suzuki–Miyaura coupling reaction and an innovative avenue for catalyst recycling and product isolation.
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spelling pubmed-92449002022-07-01 Proof of Concept: Interface of Recyclable Organogels with Embedded Palladium Nanoparticles Catalyzing Suzuki–Miyaura Coupling in Water at Room Temperature Roy Chowdhury, Srayoshi Nandi, Sujay Kumar Haldar, Debasish ACS Omega [Image: see text] A sustainable approach for C–C cross-coupling reaction at room temperature in water has been developed to avoid tedious Pd separation, reduce the carbon footprint, and save energy. Another important aspect is the catalyst recycling and easy product separation. α,γ-Hybrid peptides were designed to selectively use as a ligand for C–C cross-coupling catalysts as well as to form organogels. The peptides form antiparallel sheet-like structures in the solid state. The peptide containing m-aminobenzoic acid, glycine, and dimethylamine forms a whitish gel in toluene, and co-gelation with Pd(OAc)(2) results in light brown gel, which acts as a biphasic catalyst for Suzuki–Miyaura cross-coupling at room temperature in water by mild shaking. The organic–inorganic hybrid gel was characterized by rheology, field-emission scanning electron microscopy, transmission electron microscopy, and energy-dispersive X-ray analyses. On completion of the cross-coupling reaction, the basic aqueous layer (containing products) above the gel can be simply decanted and the intact organic–inorganic hybrid gel can be recycled by topping-up fresh reactants multiple times. The reaction permitted a range of different substitution patterns for aryl and heterocyclic halides with acid or phenol functional groups. Both electron-donating- and electron-withdrawing-substituted substrates exhibited good results for this transformation. The findings inspire toward a holistic green technology for Suzuki–Miyaura coupling reaction and an innovative avenue for catalyst recycling and product isolation. American Chemical Society 2022-06-14 /pmc/articles/PMC9244900/ /pubmed/35785310 http://dx.doi.org/10.1021/acsomega.2c01360 Text en © 2022 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by-nc-nd/4.0/Permits non-commercial access and re-use, provided that author attribution and integrity are maintained; but does not permit creation of adaptations or other derivative works (https://creativecommons.org/licenses/by-nc-nd/4.0/).
spellingShingle Roy Chowdhury, Srayoshi
Nandi, Sujay Kumar
Haldar, Debasish
Proof of Concept: Interface of Recyclable Organogels with Embedded Palladium Nanoparticles Catalyzing Suzuki–Miyaura Coupling in Water at Room Temperature
title Proof of Concept: Interface of Recyclable Organogels with Embedded Palladium Nanoparticles Catalyzing Suzuki–Miyaura Coupling in Water at Room Temperature
title_full Proof of Concept: Interface of Recyclable Organogels with Embedded Palladium Nanoparticles Catalyzing Suzuki–Miyaura Coupling in Water at Room Temperature
title_fullStr Proof of Concept: Interface of Recyclable Organogels with Embedded Palladium Nanoparticles Catalyzing Suzuki–Miyaura Coupling in Water at Room Temperature
title_full_unstemmed Proof of Concept: Interface of Recyclable Organogels with Embedded Palladium Nanoparticles Catalyzing Suzuki–Miyaura Coupling in Water at Room Temperature
title_short Proof of Concept: Interface of Recyclable Organogels with Embedded Palladium Nanoparticles Catalyzing Suzuki–Miyaura Coupling in Water at Room Temperature
title_sort proof of concept: interface of recyclable organogels with embedded palladium nanoparticles catalyzing suzuki–miyaura coupling in water at room temperature
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9244900/
https://www.ncbi.nlm.nih.gov/pubmed/35785310
http://dx.doi.org/10.1021/acsomega.2c01360
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