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A flexible approach to Pd-catalyzed carbonylations via aroyl dimethylaminopyridinium salts
4-Dimethylaminopyridine (DMAP) is shown to undergo Pd/P(t)Bu(3) catalyzed coupling with aryl halides and carbon monoxide to form electrophilic aroyl–DMAP salts. The reaction is easily scalable to prepare multigram quantities with low catalyst loadings, while the precipitation of these salts as they...
Autores principales: | , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Royal Society of Chemistry
2016
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5952522/ https://www.ncbi.nlm.nih.gov/pubmed/29861983 http://dx.doi.org/10.1039/c5sc02949j |
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author | Quesnel, Jeffrey S. Fabrikant, Alexander Arndtsen, Bruce A. |
author_facet | Quesnel, Jeffrey S. Fabrikant, Alexander Arndtsen, Bruce A. |
author_sort | Quesnel, Jeffrey S. |
collection | PubMed |
description | 4-Dimethylaminopyridine (DMAP) is shown to undergo Pd/P(t)Bu(3) catalyzed coupling with aryl halides and carbon monoxide to form electrophilic aroyl–DMAP salts. The reaction is easily scalable to prepare multigram quantities with low catalyst loadings, while the precipitation of these salts as they form leads to products with low impurities. These reagents rapidly react with a variety of nucleophiles, including those that contain potentially incompatible functional groups under standard carbonylative conditions. |
format | Online Article Text |
id | pubmed-5952522 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2016 |
publisher | Royal Society of Chemistry |
record_format | MEDLINE/PubMed |
spelling | pubmed-59525222018-06-01 A flexible approach to Pd-catalyzed carbonylations via aroyl dimethylaminopyridinium salts Quesnel, Jeffrey S. Fabrikant, Alexander Arndtsen, Bruce A. Chem Sci Chemistry 4-Dimethylaminopyridine (DMAP) is shown to undergo Pd/P(t)Bu(3) catalyzed coupling with aryl halides and carbon monoxide to form electrophilic aroyl–DMAP salts. The reaction is easily scalable to prepare multigram quantities with low catalyst loadings, while the precipitation of these salts as they form leads to products with low impurities. These reagents rapidly react with a variety of nucleophiles, including those that contain potentially incompatible functional groups under standard carbonylative conditions. Royal Society of Chemistry 2016-01-01 2015-09-30 /pmc/articles/PMC5952522/ /pubmed/29861983 http://dx.doi.org/10.1039/c5sc02949j Text en This journal is © The Royal Society of Chemistry 2016 http://creativecommons.org/licenses/by-nc/3.0/ This article is freely available. This article is licensed under a Creative Commons Attribution Non Commercial 3.0 Unported Licence (CC BY-NC 3.0) |
spellingShingle | Chemistry Quesnel, Jeffrey S. Fabrikant, Alexander Arndtsen, Bruce A. A flexible approach to Pd-catalyzed carbonylations via aroyl dimethylaminopyridinium salts |
title | A flexible approach to Pd-catalyzed carbonylations via aroyl dimethylaminopyridinium salts
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title_full | A flexible approach to Pd-catalyzed carbonylations via aroyl dimethylaminopyridinium salts
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title_fullStr | A flexible approach to Pd-catalyzed carbonylations via aroyl dimethylaminopyridinium salts
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title_full_unstemmed | A flexible approach to Pd-catalyzed carbonylations via aroyl dimethylaminopyridinium salts
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title_short | A flexible approach to Pd-catalyzed carbonylations via aroyl dimethylaminopyridinium salts
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title_sort | flexible approach to pd-catalyzed carbonylations via aroyl dimethylaminopyridinium salts |
topic | Chemistry |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5952522/ https://www.ncbi.nlm.nih.gov/pubmed/29861983 http://dx.doi.org/10.1039/c5sc02949j |
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