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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...
Autores principales: | , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
American Chemical Society
2022
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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. |
format | Online Article Text |
id | pubmed-9244900 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2022 |
publisher | American Chemical Society |
record_format | MEDLINE/PubMed |
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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