Cargando…
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...
Autores principales: | , , , , |
---|---|
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 |
_version_ | 1783292240565633024 |
---|---|
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. |
format | Online Article Text |
id | pubmed-5765485 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2017 |
publisher | John Wiley and Sons Inc. |
record_format | MEDLINE/PubMed |
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 |
work_keys_str_mv | AT donneradrian hybridsurfactantswithnheterocycliccarbeneheadsasamultifunctionalplatformforinterfacialcatalysis AT hagedornkay hybridsurfactantswithnheterocycliccarbeneheadsasamultifunctionalplatformforinterfacialcatalysis AT matteslorenz hybridsurfactantswithnheterocycliccarbeneheadsasamultifunctionalplatformforinterfacialcatalysis AT drechslermarkus hybridsurfactantswithnheterocycliccarbeneheadsasamultifunctionalplatformforinterfacialcatalysis AT polarzsebastian hybridsurfactantswithnheterocycliccarbeneheadsasamultifunctionalplatformforinterfacialcatalysis |