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Hybrid Surfactants with N‐Heterocyclic Carbene Heads as a Multifunctional Platform for Interfacial Catalysis

Processing of substrates with different solvent compatibility is a persistent problem in homogeneous catalysis, in particular when one starting compound is water soluble and the other is not. A promising concept reported in the literature is micellar catalysis. However, the process of developing cat...

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Autores principales: Donner, Adrian, Hagedorn, Kay, Mattes, Lorenz, Drechsler, Markus, Polarz, Sebastian
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2017
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5765485/
https://www.ncbi.nlm.nih.gov/pubmed/28940413
http://dx.doi.org/10.1002/chem.201703902
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author Donner, Adrian
Hagedorn, Kay
Mattes, Lorenz
Drechsler, Markus
Polarz, Sebastian
author_facet Donner, Adrian
Hagedorn, Kay
Mattes, Lorenz
Drechsler, Markus
Polarz, Sebastian
author_sort Donner, Adrian
collection PubMed
description Processing of substrates with different solvent compatibility is a persistent problem in homogeneous catalysis, in particular when one starting compound is water soluble and the other is not. A promising concept reported in the literature is micellar catalysis. However, the process of developing catalysts that are surfactants at the same time is still in its early stages. We report the synthesis of a new surfactant system with an N‐heterocyclic carbene (NHC) moiety as a head group. Characteristic surfactant properties such as the formation of micelles or liquid crystals is documented. The new surfactant ligand forms coordination compounds with various metals, most importantly Pd(2+), in square planar geometry. In addition, the Pd‐NHC compound shows surfactant features, and can be used successfully for C−C cross‐coupling reactions (Suzuki, Heck). The boost in catalytic activity by one order of magnitude compared to analogous but non‐amphiphilic species is reported.
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spelling pubmed-57654852018-02-01 Hybrid Surfactants with N‐Heterocyclic Carbene Heads as a Multifunctional Platform for Interfacial Catalysis Donner, Adrian Hagedorn, Kay Mattes, Lorenz Drechsler, Markus Polarz, Sebastian Chemistry Communications Processing of substrates with different solvent compatibility is a persistent problem in homogeneous catalysis, in particular when one starting compound is water soluble and the other is not. A promising concept reported in the literature is micellar catalysis. However, the process of developing catalysts that are surfactants at the same time is still in its early stages. We report the synthesis of a new surfactant system with an N‐heterocyclic carbene (NHC) moiety as a head group. Characteristic surfactant properties such as the formation of micelles or liquid crystals is documented. The new surfactant ligand forms coordination compounds with various metals, most importantly Pd(2+), in square planar geometry. In addition, the Pd‐NHC compound shows surfactant features, and can be used successfully for C−C cross‐coupling reactions (Suzuki, Heck). The boost in catalytic activity by one order of magnitude compared to analogous but non‐amphiphilic species is reported. John Wiley and Sons Inc. 2017-10-18 2017-12-22 /pmc/articles/PMC5765485/ /pubmed/28940413 http://dx.doi.org/10.1002/chem.201703902 Text en © 2017 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution‐NonCommercial‐NoDerivs (http://creativecommons.org/licenses/by-nc-nd/4.0/) License, which permits use and distribution in any medium, provided the original work is properly cited, the use is non‐commercial and no modifications or adaptations are made.
spellingShingle Communications
Donner, Adrian
Hagedorn, Kay
Mattes, Lorenz
Drechsler, Markus
Polarz, Sebastian
Hybrid Surfactants with N‐Heterocyclic Carbene Heads as a Multifunctional Platform for Interfacial Catalysis
title Hybrid Surfactants with N‐Heterocyclic Carbene Heads as a Multifunctional Platform for Interfacial Catalysis
title_full Hybrid Surfactants with N‐Heterocyclic Carbene Heads as a Multifunctional Platform for Interfacial Catalysis
title_fullStr Hybrid Surfactants with N‐Heterocyclic Carbene Heads as a Multifunctional Platform for Interfacial Catalysis
title_full_unstemmed Hybrid Surfactants with N‐Heterocyclic Carbene Heads as a Multifunctional Platform for Interfacial Catalysis
title_short Hybrid Surfactants with N‐Heterocyclic Carbene Heads as a Multifunctional Platform for Interfacial Catalysis
title_sort hybrid surfactants with n‐heterocyclic carbene heads as a multifunctional platform for interfacial catalysis
topic Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5765485/
https://www.ncbi.nlm.nih.gov/pubmed/28940413
http://dx.doi.org/10.1002/chem.201703902
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