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Translation of microwave methodology to continuous flow for the efficient synthesis of diaryl ethers via a base-mediated S(N)Ar reaction
Whilst microwave heating has been widely demonstrated as a synthetically useful tool for rapid reaction screening, a microwave-absorbing solvent is often required in order to achieve efficient reactant heating. In comparison, microreactors can be readily heated and pressurised in order to “super-hea...
Autores principales: | , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Beilstein-Institut
2011
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3201050/ https://www.ncbi.nlm.nih.gov/pubmed/22043247 http://dx.doi.org/10.3762/bjoc.7.160 |
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author | Wiles, Charlotte Watts, Paul |
author_facet | Wiles, Charlotte Watts, Paul |
author_sort | Wiles, Charlotte |
collection | PubMed |
description | Whilst microwave heating has been widely demonstrated as a synthetically useful tool for rapid reaction screening, a microwave-absorbing solvent is often required in order to achieve efficient reactant heating. In comparison, microreactors can be readily heated and pressurised in order to “super-heat” the reaction mixture, meaning that microwave-transparent solvents can also be employed. To demonstrate the advantages associated with microreaction technology a series of S(N)Ar reactions were performed under continuous flow by following previously developed microwave protocols as a starting point for the investigation. By this approach, an automated microreaction platform (Labtrix(®) S1) was employed for the continuous flow synthesis of diaryl ethers at 195 °C and 25 bar, affording a reduction in reaction time from tens of minutes to 60 s when compared with a stopped-flow microwave reactor. |
format | Online Article Text |
id | pubmed-3201050 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2011 |
publisher | Beilstein-Institut |
record_format | MEDLINE/PubMed |
spelling | pubmed-32010502011-10-31 Translation of microwave methodology to continuous flow for the efficient synthesis of diaryl ethers via a base-mediated S(N)Ar reaction Wiles, Charlotte Watts, Paul Beilstein J Org Chem Full Research Paper Whilst microwave heating has been widely demonstrated as a synthetically useful tool for rapid reaction screening, a microwave-absorbing solvent is often required in order to achieve efficient reactant heating. In comparison, microreactors can be readily heated and pressurised in order to “super-heat” the reaction mixture, meaning that microwave-transparent solvents can also be employed. To demonstrate the advantages associated with microreaction technology a series of S(N)Ar reactions were performed under continuous flow by following previously developed microwave protocols as a starting point for the investigation. By this approach, an automated microreaction platform (Labtrix(®) S1) was employed for the continuous flow synthesis of diaryl ethers at 195 °C and 25 bar, affording a reduction in reaction time from tens of minutes to 60 s when compared with a stopped-flow microwave reactor. Beilstein-Institut 2011-10-04 /pmc/articles/PMC3201050/ /pubmed/22043247 http://dx.doi.org/10.3762/bjoc.7.160 Text en Copyright © 2011, Wiles and Watts https://creativecommons.org/licenses/by/2.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms) |
spellingShingle | Full Research Paper Wiles, Charlotte Watts, Paul Translation of microwave methodology to continuous flow for the efficient synthesis of diaryl ethers via a base-mediated S(N)Ar reaction |
title | Translation of microwave methodology to continuous flow for the efficient synthesis of diaryl ethers via a base-mediated S(N)Ar reaction |
title_full | Translation of microwave methodology to continuous flow for the efficient synthesis of diaryl ethers via a base-mediated S(N)Ar reaction |
title_fullStr | Translation of microwave methodology to continuous flow for the efficient synthesis of diaryl ethers via a base-mediated S(N)Ar reaction |
title_full_unstemmed | Translation of microwave methodology to continuous flow for the efficient synthesis of diaryl ethers via a base-mediated S(N)Ar reaction |
title_short | Translation of microwave methodology to continuous flow for the efficient synthesis of diaryl ethers via a base-mediated S(N)Ar reaction |
title_sort | translation of microwave methodology to continuous flow for the efficient synthesis of diaryl ethers via a base-mediated s(n)ar reaction |
topic | Full Research Paper |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3201050/ https://www.ncbi.nlm.nih.gov/pubmed/22043247 http://dx.doi.org/10.3762/bjoc.7.160 |
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