Cargando…

Disposable cartridge concept for the on-demand synthesis of turbo Grignards, Knochel–Hauser amides, and magnesium alkoxides

Magnesium organometallic reagents occupy a central position in organic synthesis. The freshness of these compounds is the key for achieving a high conversion and reproducible results. Common methods for the synthesis of Grignard reagents from metallic magnesium present safety issues and exhibit a ba...

Descripción completa

Detalles Bibliográficos
Autores principales: Berton, Mateo, Sheehan, Kevin, Adamo, Andrea, McQuade, D Tyler
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2020
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7308606/
https://www.ncbi.nlm.nih.gov/pubmed/32595782
http://dx.doi.org/10.3762/bjoc.16.115
_version_ 1783549027311157248
author Berton, Mateo
Sheehan, Kevin
Adamo, Andrea
McQuade, D Tyler
author_facet Berton, Mateo
Sheehan, Kevin
Adamo, Andrea
McQuade, D Tyler
author_sort Berton, Mateo
collection PubMed
description Magnesium organometallic reagents occupy a central position in organic synthesis. The freshness of these compounds is the key for achieving a high conversion and reproducible results. Common methods for the synthesis of Grignard reagents from metallic magnesium present safety issues and exhibit a batch-to-batch variability. Tubular reactors of solid reagents combined with solution-phase reagents enable the continuous-flow preparation of organomagnesium reagents. The use of stratified packed-bed columns of magnesium metal and lithium chloride for the synthesis of highly concentrated turbo Grignards is reported. A low-cost pod-style synthesizer prototype, which incorporates single-use prepacked perfluorinated cartridges and bags of reagents for the automated on-demand lab-scale synthesis of carbon, nitrogen, and oxygen turbo magnesium bases is presented. This concept will provide access to fresh organomagnesium reagents on a discovery scale and will do so independent from the operator’s experience in flow and/or organometallic chemistry.
format Online
Article
Text
id pubmed-7308606
institution National Center for Biotechnology Information
language English
publishDate 2020
publisher Beilstein-Institut
record_format MEDLINE/PubMed
spelling pubmed-73086062020-06-25 Disposable cartridge concept for the on-demand synthesis of turbo Grignards, Knochel–Hauser amides, and magnesium alkoxides Berton, Mateo Sheehan, Kevin Adamo, Andrea McQuade, D Tyler Beilstein J Org Chem Full Research Paper Magnesium organometallic reagents occupy a central position in organic synthesis. The freshness of these compounds is the key for achieving a high conversion and reproducible results. Common methods for the synthesis of Grignard reagents from metallic magnesium present safety issues and exhibit a batch-to-batch variability. Tubular reactors of solid reagents combined with solution-phase reagents enable the continuous-flow preparation of organomagnesium reagents. The use of stratified packed-bed columns of magnesium metal and lithium chloride for the synthesis of highly concentrated turbo Grignards is reported. A low-cost pod-style synthesizer prototype, which incorporates single-use prepacked perfluorinated cartridges and bags of reagents for the automated on-demand lab-scale synthesis of carbon, nitrogen, and oxygen turbo magnesium bases is presented. This concept will provide access to fresh organomagnesium reagents on a discovery scale and will do so independent from the operator’s experience in flow and/or organometallic chemistry. Beilstein-Institut 2020-06-19 /pmc/articles/PMC7308606/ /pubmed/32595782 http://dx.doi.org/10.3762/bjoc.16.115 Text en Copyright © 2020, Berton et al. https://creativecommons.org/licenses/by/4.0https://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/4.0). Please note that the reuse, redistribution and reproduction in particular requires that the authors and source are credited. 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
Berton, Mateo
Sheehan, Kevin
Adamo, Andrea
McQuade, D Tyler
Disposable cartridge concept for the on-demand synthesis of turbo Grignards, Knochel–Hauser amides, and magnesium alkoxides
title Disposable cartridge concept for the on-demand synthesis of turbo Grignards, Knochel–Hauser amides, and magnesium alkoxides
title_full Disposable cartridge concept for the on-demand synthesis of turbo Grignards, Knochel–Hauser amides, and magnesium alkoxides
title_fullStr Disposable cartridge concept for the on-demand synthesis of turbo Grignards, Knochel–Hauser amides, and magnesium alkoxides
title_full_unstemmed Disposable cartridge concept for the on-demand synthesis of turbo Grignards, Knochel–Hauser amides, and magnesium alkoxides
title_short Disposable cartridge concept for the on-demand synthesis of turbo Grignards, Knochel–Hauser amides, and magnesium alkoxides
title_sort disposable cartridge concept for the on-demand synthesis of turbo grignards, knochel–hauser amides, and magnesium alkoxides
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7308606/
https://www.ncbi.nlm.nih.gov/pubmed/32595782
http://dx.doi.org/10.3762/bjoc.16.115
work_keys_str_mv AT bertonmateo disposablecartridgeconceptfortheondemandsynthesisofturbogrignardsknochelhauseramidesandmagnesiumalkoxides
AT sheehankevin disposablecartridgeconceptfortheondemandsynthesisofturbogrignardsknochelhauseramidesandmagnesiumalkoxides
AT adamoandrea disposablecartridgeconceptfortheondemandsynthesisofturbogrignardsknochelhauseramidesandmagnesiumalkoxides
AT mcquadedtyler disposablecartridgeconceptfortheondemandsynthesisofturbogrignardsknochelhauseramidesandmagnesiumalkoxides