Continuous Flow Sodiation of Substituted Acrylonitriles, Alkenyl Sulfides and Acrylates

The sodiation of substituted acrylonitriles and alkenyl sulfides in a continuous flow set‐up using NaDA (sodium diisopropylamide) in EtNMe(2) or NaTMP (sodium 2,2,6,6‐tetramethylpiperidide)⋅TMEDA in n‐hexane provides sodiated acrylonitriles and alkenyl sulfides, which are subsequently trapped in bat...

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Autores principales: Harenberg, Johannes H., Weidmann, Niels, Karaghiosoff, Konstantin, Knochel, Paul
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2020
Materias:
Communications
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7821005/
https://www.ncbi.nlm.nih.gov/pubmed/33026681
http://dx.doi.org/10.1002/anie.202012085
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author Harenberg, Johannes H.
Weidmann, Niels
Karaghiosoff, Konstantin
Knochel, Paul
author_facet Harenberg, Johannes H.
Weidmann, Niels
Karaghiosoff, Konstantin
Knochel, Paul
author_sort Harenberg, Johannes H.
collection PubMed
description The sodiation of substituted acrylonitriles and alkenyl sulfides in a continuous flow set‐up using NaDA (sodium diisopropylamide) in EtNMe(2) or NaTMP (sodium 2,2,6,6‐tetramethylpiperidide)⋅TMEDA in n‐hexane provides sodiated acrylonitriles and alkenyl sulfides, which are subsequently trapped in batch with various electrophiles such as aldehydes, ketones, disulfides and allylic bromides affording functionalized acrylonitriles and alkenyl sulfides. This flow‐procedure was successfully extended to other acrylates by using Barbier‐type conditions.
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spelling pubmed-78210052021-01-26 Continuous Flow Sodiation of Substituted Acrylonitriles, Alkenyl Sulfides and Acrylates Harenberg, Johannes H. Weidmann, Niels Karaghiosoff, Konstantin Knochel, Paul Angew Chem Int Ed Engl Communications The sodiation of substituted acrylonitriles and alkenyl sulfides in a continuous flow set‐up using NaDA (sodium diisopropylamide) in EtNMe(2) or NaTMP (sodium 2,2,6,6‐tetramethylpiperidide)⋅TMEDA in n‐hexane provides sodiated acrylonitriles and alkenyl sulfides, which are subsequently trapped in batch with various electrophiles such as aldehydes, ketones, disulfides and allylic bromides affording functionalized acrylonitriles and alkenyl sulfides. This flow‐procedure was successfully extended to other acrylates by using Barbier‐type conditions. John Wiley and Sons Inc. 2020-11-03 2021-01-11 /pmc/articles/PMC7821005/ /pubmed/33026681 http://dx.doi.org/10.1002/anie.202012085 Text en © 2020 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH This is an open access article under the terms of the http://creativecommons.org/licenses/by/4.0/ License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
spellingShingle Communications
Harenberg, Johannes H.
Weidmann, Niels
Karaghiosoff, Konstantin
Knochel, Paul
Continuous Flow Sodiation of Substituted Acrylonitriles, Alkenyl Sulfides and Acrylates
title Continuous Flow Sodiation of Substituted Acrylonitriles, Alkenyl Sulfides and Acrylates
title_full Continuous Flow Sodiation of Substituted Acrylonitriles, Alkenyl Sulfides and Acrylates
title_fullStr Continuous Flow Sodiation of Substituted Acrylonitriles, Alkenyl Sulfides and Acrylates
title_full_unstemmed Continuous Flow Sodiation of Substituted Acrylonitriles, Alkenyl Sulfides and Acrylates
title_short Continuous Flow Sodiation of Substituted Acrylonitriles, Alkenyl Sulfides and Acrylates
title_sort continuous flow sodiation of substituted acrylonitriles, alkenyl sulfides and acrylates
topic Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7821005/
https://www.ncbi.nlm.nih.gov/pubmed/33026681
http://dx.doi.org/10.1002/anie.202012085
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