Organomagnesium Based Flash Chemistry: Continuous Flow Generation and Utilization of Halomethylmagnesium Intermediates

[Image: see text] The generation of highly unstable chloromethylmagnesium chloride in a continuous flow reactor and its reaction with aldehydes and ketones is reported. With this strategy, chlorohydrins and epoxides were synthesized within a total residence time of only 2.6 s. The outcome of the rea...

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Autores principales: von Keutz, Timo, Cantillo, David, Kappe, C. Oliver
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2020
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7586391/
https://www.ncbi.nlm.nih.gov/pubmed/32914630
http://dx.doi.org/10.1021/acs.orglett.0c02725
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author von Keutz, Timo
Cantillo, David
Kappe, C. Oliver
author_facet von Keutz, Timo
Cantillo, David
Kappe, C. Oliver
author_sort von Keutz, Timo
collection PubMed
description [Image: see text] The generation of highly unstable chloromethylmagnesium chloride in a continuous flow reactor and its reaction with aldehydes and ketones is reported. With this strategy, chlorohydrins and epoxides were synthesized within a total residence time of only 2.6 s. The outcome of the reaction can be tuned by simply using either a basic or an acidic quench. Very good to excellent isolated yields, up to 97%, have been obtained for most cases (30 examples).
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spelling pubmed-75863912020-10-27 Organomagnesium Based Flash Chemistry: Continuous Flow Generation and Utilization of Halomethylmagnesium Intermediates von Keutz, Timo Cantillo, David Kappe, C. Oliver Org Lett [Image: see text] The generation of highly unstable chloromethylmagnesium chloride in a continuous flow reactor and its reaction with aldehydes and ketones is reported. With this strategy, chlorohydrins and epoxides were synthesized within a total residence time of only 2.6 s. The outcome of the reaction can be tuned by simply using either a basic or an acidic quench. Very good to excellent isolated yields, up to 97%, have been obtained for most cases (30 examples). American Chemical Society 2020-09-11 2020-10-02 /pmc/articles/PMC7586391/ /pubmed/32914630 http://dx.doi.org/10.1021/acs.orglett.0c02725 Text en This is an open access article published under a Creative Commons Attribution (CC-BY) License (http://pubs.acs.org/page/policy/authorchoice_ccby_termsofuse.html) , which permits unrestricted use, distribution and reproduction in any medium, provided the author and source are cited.
spellingShingle von Keutz, Timo
Cantillo, David
Kappe, C. Oliver
Organomagnesium Based Flash Chemistry: Continuous Flow Generation and Utilization of Halomethylmagnesium Intermediates
title Organomagnesium Based Flash Chemistry: Continuous Flow Generation and Utilization of Halomethylmagnesium Intermediates
title_full Organomagnesium Based Flash Chemistry: Continuous Flow Generation and Utilization of Halomethylmagnesium Intermediates
title_fullStr Organomagnesium Based Flash Chemistry: Continuous Flow Generation and Utilization of Halomethylmagnesium Intermediates
title_full_unstemmed Organomagnesium Based Flash Chemistry: Continuous Flow Generation and Utilization of Halomethylmagnesium Intermediates
title_short Organomagnesium Based Flash Chemistry: Continuous Flow Generation and Utilization of Halomethylmagnesium Intermediates
title_sort organomagnesium based flash chemistry: continuous flow generation and utilization of halomethylmagnesium intermediates
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7586391/
https://www.ncbi.nlm.nih.gov/pubmed/32914630
http://dx.doi.org/10.1021/acs.orglett.0c02725
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