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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...

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Autores principales: Teskey, Christopher J., Adler, Pauline, Gonçalves, Carlos R., Maulide, Nuno
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2018
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.
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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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