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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...

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Detalles Bibliográficos
Autores principales: Quesnel, Jeffrey S., Fabrikant, Alexander, Arndtsen, Bruce A.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Royal Society of Chemistry 2016
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.
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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
title_full A flexible approach to Pd-catalyzed carbonylations via aroyl dimethylaminopyridinium salts
title_fullStr A flexible approach to Pd-catalyzed carbonylations via aroyl dimethylaminopyridinium salts
title_full_unstemmed A flexible approach to Pd-catalyzed carbonylations via aroyl dimethylaminopyridinium salts
title_short A flexible approach to Pd-catalyzed carbonylations via aroyl dimethylaminopyridinium salts
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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