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α‐Functionalisation of Ketones Through Metal‐Free Electrophilic Activation
Triflic anhydride mediated activation of acetophenones leads to highly electrophilic intermediates that can undergo a variety of transformations when treated with nucleophiles. This electrophilic ketone activation gives access to α‐arylated and α‐oxyaminated acetophenones under metal‐free conditions...
Autores principales: | , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
John Wiley and Sons Inc.
2020
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7693173/ https://www.ncbi.nlm.nih.gov/pubmed/32914929 http://dx.doi.org/10.1002/anie.202006398 |
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author | Zawodny, Wojciech Teskey, Christopher J. Mishevska, Magdalena Völkl, Martin Maryasin, Boris González, Leticia Maulide, Nuno |
author_facet | Zawodny, Wojciech Teskey, Christopher J. Mishevska, Magdalena Völkl, Martin Maryasin, Boris González, Leticia Maulide, Nuno |
author_sort | Zawodny, Wojciech |
collection | PubMed |
description | Triflic anhydride mediated activation of acetophenones leads to highly electrophilic intermediates that can undergo a variety of transformations when treated with nucleophiles. This electrophilic ketone activation gives access to α‐arylated and α‐oxyaminated acetophenones under metal‐free conditions in moderate to excellent yields and enables extension to the synthesis of arylated morpholines via generation of vinylsulfonium salts. Computational investigations confirmed the transient existence of intermediates derived from vinyl triflates and the role of the oxygen atoms at the para position of aromatic ring in facilitating their stabilisation. |
format | Online Article Text |
id | pubmed-7693173 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2020 |
publisher | John Wiley and Sons Inc. |
record_format | MEDLINE/PubMed |
spelling | pubmed-76931732020-12-11 α‐Functionalisation of Ketones Through Metal‐Free Electrophilic Activation Zawodny, Wojciech Teskey, Christopher J. Mishevska, Magdalena Völkl, Martin Maryasin, Boris González, Leticia Maulide, Nuno Angew Chem Int Ed Engl Communications Triflic anhydride mediated activation of acetophenones leads to highly electrophilic intermediates that can undergo a variety of transformations when treated with nucleophiles. This electrophilic ketone activation gives access to α‐arylated and α‐oxyaminated acetophenones under metal‐free conditions in moderate to excellent yields and enables extension to the synthesis of arylated morpholines via generation of vinylsulfonium salts. Computational investigations confirmed the transient existence of intermediates derived from vinyl triflates and the role of the oxygen atoms at the para position of aromatic ring in facilitating their stabilisation. John Wiley and Sons Inc. 2020-09-11 2020-11-16 /pmc/articles/PMC7693173/ /pubmed/32914929 http://dx.doi.org/10.1002/anie.202006398 Text en © 2020 The Authors. 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 Zawodny, Wojciech Teskey, Christopher J. Mishevska, Magdalena Völkl, Martin Maryasin, Boris González, Leticia Maulide, Nuno α‐Functionalisation of Ketones Through Metal‐Free Electrophilic Activation |
title | α‐Functionalisation of Ketones Through Metal‐Free Electrophilic Activation |
title_full | α‐Functionalisation of Ketones Through Metal‐Free Electrophilic Activation |
title_fullStr | α‐Functionalisation of Ketones Through Metal‐Free Electrophilic Activation |
title_full_unstemmed | α‐Functionalisation of Ketones Through Metal‐Free Electrophilic Activation |
title_short | α‐Functionalisation of Ketones Through Metal‐Free Electrophilic Activation |
title_sort | α‐functionalisation of ketones through metal‐free electrophilic activation |
topic | Communications |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7693173/ https://www.ncbi.nlm.nih.gov/pubmed/32914929 http://dx.doi.org/10.1002/anie.202006398 |
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