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Decarboxylation and Tandem Reduction/Decarboxylation Pathways to Substituted Phenols from Aromatic Carboxylic Acids Using Bimetallic Nanoparticles on Supported Ionic Liquid Phases as Multifunctional Catalysts

[Image: see text] Valuable substituted phenols are accessible via the selective decarboxylation of hydroxybenzoic acid derivatives using multifunctional catalysts composed of bimetallic iron–ruthenium nanoparticles immobilized on an amine-functionalized supported ionic liquid phase (Fe(25)Ru(75)@SIL...

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Autores principales: Levin, Natalia, Goclik, Lisa, Walschus, Henrik, Antil, Neha, Bordet, Alexis, Leitner, Walter
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2023
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10591467/
https://www.ncbi.nlm.nih.gov/pubmed/37815193
http://dx.doi.org/10.1021/jacs.3c09290
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author Levin, Natalia
Goclik, Lisa
Walschus, Henrik
Antil, Neha
Bordet, Alexis
Leitner, Walter
author_facet Levin, Natalia
Goclik, Lisa
Walschus, Henrik
Antil, Neha
Bordet, Alexis
Leitner, Walter
author_sort Levin, Natalia
collection PubMed
description [Image: see text] Valuable substituted phenols are accessible via the selective decarboxylation of hydroxybenzoic acid derivatives using multifunctional catalysts composed of bimetallic iron–ruthenium nanoparticles immobilized on an amine-functionalized supported ionic liquid phase (Fe(25)Ru(75)@SILP+IL-NEt(2)). The individual components of the catalytic system are assembled using a molecular approach to bring metal and amine sites into close contact on the support material, providing high stability and high decarboxylation activity. Operating under a hydrogen atmosphere was found to be essential to achieve high selectivity and yields. As the catalyst materials enable also the selective hydrogenation and hydrodeoxygenation of various additional functional groups (i.e., formyl, acyl, and nitro substituents), direct access to the corresponding phenols can be achieved via integrated tandem reactions. The approach opens versatile synthetic pathways for the production of valuable phenols from a wide range of readily available substrates, including compounds derived from lignocellulosic biomass.
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spelling pubmed-105914672023-10-24 Decarboxylation and Tandem Reduction/Decarboxylation Pathways to Substituted Phenols from Aromatic Carboxylic Acids Using Bimetallic Nanoparticles on Supported Ionic Liquid Phases as Multifunctional Catalysts Levin, Natalia Goclik, Lisa Walschus, Henrik Antil, Neha Bordet, Alexis Leitner, Walter J Am Chem Soc [Image: see text] Valuable substituted phenols are accessible via the selective decarboxylation of hydroxybenzoic acid derivatives using multifunctional catalysts composed of bimetallic iron–ruthenium nanoparticles immobilized on an amine-functionalized supported ionic liquid phase (Fe(25)Ru(75)@SILP+IL-NEt(2)). The individual components of the catalytic system are assembled using a molecular approach to bring metal and amine sites into close contact on the support material, providing high stability and high decarboxylation activity. Operating under a hydrogen atmosphere was found to be essential to achieve high selectivity and yields. As the catalyst materials enable also the selective hydrogenation and hydrodeoxygenation of various additional functional groups (i.e., formyl, acyl, and nitro substituents), direct access to the corresponding phenols can be achieved via integrated tandem reactions. The approach opens versatile synthetic pathways for the production of valuable phenols from a wide range of readily available substrates, including compounds derived from lignocellulosic biomass. American Chemical Society 2023-10-10 /pmc/articles/PMC10591467/ /pubmed/37815193 http://dx.doi.org/10.1021/jacs.3c09290 Text en © 2023 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Levin, Natalia
Goclik, Lisa
Walschus, Henrik
Antil, Neha
Bordet, Alexis
Leitner, Walter
Decarboxylation and Tandem Reduction/Decarboxylation Pathways to Substituted Phenols from Aromatic Carboxylic Acids Using Bimetallic Nanoparticles on Supported Ionic Liquid Phases as Multifunctional Catalysts
title Decarboxylation and Tandem Reduction/Decarboxylation Pathways to Substituted Phenols from Aromatic Carboxylic Acids Using Bimetallic Nanoparticles on Supported Ionic Liquid Phases as Multifunctional Catalysts
title_full Decarboxylation and Tandem Reduction/Decarboxylation Pathways to Substituted Phenols from Aromatic Carboxylic Acids Using Bimetallic Nanoparticles on Supported Ionic Liquid Phases as Multifunctional Catalysts
title_fullStr Decarboxylation and Tandem Reduction/Decarboxylation Pathways to Substituted Phenols from Aromatic Carboxylic Acids Using Bimetallic Nanoparticles on Supported Ionic Liquid Phases as Multifunctional Catalysts
title_full_unstemmed Decarboxylation and Tandem Reduction/Decarboxylation Pathways to Substituted Phenols from Aromatic Carboxylic Acids Using Bimetallic Nanoparticles on Supported Ionic Liquid Phases as Multifunctional Catalysts
title_short Decarboxylation and Tandem Reduction/Decarboxylation Pathways to Substituted Phenols from Aromatic Carboxylic Acids Using Bimetallic Nanoparticles on Supported Ionic Liquid Phases as Multifunctional Catalysts
title_sort decarboxylation and tandem reduction/decarboxylation pathways to substituted phenols from aromatic carboxylic acids using bimetallic nanoparticles on supported ionic liquid phases as multifunctional catalysts
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10591467/
https://www.ncbi.nlm.nih.gov/pubmed/37815193
http://dx.doi.org/10.1021/jacs.3c09290
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