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Chemoselective α,β‐Dehydrogenation of Saturated Amides
We report a method for the selective α,β‐dehydrogenation of amides in the presence of other carbonyl moieties under mild conditions. Our strategy relies on electrophilic activation coupled to in situ selective selenium‐mediated dehydrogenation. The α,β‐unsaturated products were obtained in moderate...
Autores principales: | , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
John Wiley and Sons Inc.
2018
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6348382/ https://www.ncbi.nlm.nih.gov/pubmed/30332524 http://dx.doi.org/10.1002/anie.201808794 |
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author | Teskey, Christopher J. Adler, Pauline Gonçalves, Carlos R. Maulide, Nuno |
author_facet | Teskey, Christopher J. Adler, Pauline Gonçalves, Carlos R. Maulide, Nuno |
author_sort | Teskey, Christopher J. |
collection | PubMed |
description | We report a method for the selective α,β‐dehydrogenation of amides in the presence of other carbonyl moieties under mild conditions. Our strategy relies on electrophilic activation coupled to in situ selective selenium‐mediated dehydrogenation. The α,β‐unsaturated products were obtained in moderate to excellent yields, and their synthetic versatility was demonstrated by a range of transformations. Mechanistic experiments suggest formation of an electrophilic Se(IV) species. |
format | Online Article Text |
id | pubmed-6348382 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2018 |
publisher | John Wiley and Sons Inc. |
record_format | MEDLINE/PubMed |
spelling | pubmed-63483822019-01-31 Chemoselective α,β‐Dehydrogenation of Saturated Amides Teskey, Christopher J. Adler, Pauline Gonçalves, Carlos R. Maulide, Nuno Angew Chem Int Ed Engl Communications We report a method for the selective α,β‐dehydrogenation of amides in the presence of other carbonyl moieties under mild conditions. Our strategy relies on electrophilic activation coupled to in situ selective selenium‐mediated dehydrogenation. The α,β‐unsaturated products were obtained in moderate to excellent yields, and their synthetic versatility was demonstrated by a range of transformations. Mechanistic experiments suggest formation of an electrophilic Se(IV) species. John Wiley and Sons Inc. 2018-12-07 2019-01-08 /pmc/articles/PMC6348382/ /pubmed/30332524 http://dx.doi.org/10.1002/anie.201808794 Text en © 2018 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. 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 Teskey, Christopher J. Adler, Pauline Gonçalves, Carlos R. Maulide, Nuno Chemoselective α,β‐Dehydrogenation of Saturated Amides |
title | Chemoselective α,β‐Dehydrogenation of Saturated Amides |
title_full | Chemoselective α,β‐Dehydrogenation of Saturated Amides |
title_fullStr | Chemoselective α,β‐Dehydrogenation of Saturated Amides |
title_full_unstemmed | Chemoselective α,β‐Dehydrogenation of Saturated Amides |
title_short | Chemoselective α,β‐Dehydrogenation of Saturated Amides |
title_sort | chemoselective α,β‐dehydrogenation of saturated amides |
topic | Communications |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6348382/ https://www.ncbi.nlm.nih.gov/pubmed/30332524 http://dx.doi.org/10.1002/anie.201808794 |
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