Gold(I)‐Catalyzed Nucleophilic Allylation of Azinium Ions with Allylboronates

Gold(I)‐catalyzed nucleophilic allylations of pyridinium and quinolinium ions with various allyl pinacolboronates are reported. The reactions are completely selective with respect to the site of the azinium ion that is attacked, to give various functionalized 1,4‐dihydropyridines and 1,4‐dihydroquin...

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Autores principales: O'Brien, Luke, Argent, Stephen P., Ermanis, Kristaps, Lam, Hon Wai
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2022
Materias:
Research Articles
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9314030/
https://www.ncbi.nlm.nih.gov/pubmed/35239987
http://dx.doi.org/10.1002/anie.202202305
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author O'Brien, Luke
Argent, Stephen P.
Ermanis, Kristaps
Lam, Hon Wai
author_facet O'Brien, Luke
Argent, Stephen P.
Ermanis, Kristaps
Lam, Hon Wai
author_sort O'Brien, Luke
collection PubMed
description Gold(I)‐catalyzed nucleophilic allylations of pyridinium and quinolinium ions with various allyl pinacolboronates are reported. The reactions are completely selective with respect to the site of the azinium ion that is attacked, to give various functionalized 1,4‐dihydropyridines and 1,4‐dihydroquinolines. Evidence suggests that the reactions proceed through nucleophilic allylgold(I) intermediates formed by transmetalation from allylboronates. Density functional theory (DFT) calculations provided mechanistic insight.
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spelling pubmed-93140302022-07-30 Gold(I)‐Catalyzed Nucleophilic Allylation of Azinium Ions with Allylboronates O'Brien, Luke Argent, Stephen P. Ermanis, Kristaps Lam, Hon Wai Angew Chem Int Ed Engl Research Articles Gold(I)‐catalyzed nucleophilic allylations of pyridinium and quinolinium ions with various allyl pinacolboronates are reported. The reactions are completely selective with respect to the site of the azinium ion that is attacked, to give various functionalized 1,4‐dihydropyridines and 1,4‐dihydroquinolines. Evidence suggests that the reactions proceed through nucleophilic allylgold(I) intermediates formed by transmetalation from allylboronates. Density functional theory (DFT) calculations provided mechanistic insight. John Wiley and Sons Inc. 2022-03-25 2022-05-23 /pmc/articles/PMC9314030/ /pubmed/35239987 http://dx.doi.org/10.1002/anie.202202305 Text en © 2022 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH https://creativecommons.org/licenses/by/4.0/This is an open access article under the terms of the http://creativecommons.org/licenses/by/4.0/ (https://creativecommons.org/licenses/by/4.0/) License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
spellingShingle Research Articles
O'Brien, Luke
Argent, Stephen P.
Ermanis, Kristaps
Lam, Hon Wai
Gold(I)‐Catalyzed Nucleophilic Allylation of Azinium Ions with Allylboronates
title Gold(I)‐Catalyzed Nucleophilic Allylation of Azinium Ions with Allylboronates
title_full Gold(I)‐Catalyzed Nucleophilic Allylation of Azinium Ions with Allylboronates
title_fullStr Gold(I)‐Catalyzed Nucleophilic Allylation of Azinium Ions with Allylboronates
title_full_unstemmed Gold(I)‐Catalyzed Nucleophilic Allylation of Azinium Ions with Allylboronates
title_short Gold(I)‐Catalyzed Nucleophilic Allylation of Azinium Ions with Allylboronates
title_sort gold(i)‐catalyzed nucleophilic allylation of azinium ions with allylboronates
topic Research Articles
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9314030/
https://www.ncbi.nlm.nih.gov/pubmed/35239987
http://dx.doi.org/10.1002/anie.202202305
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