NHC Catalysis for Umpolung Pyridinium Alkylation via Deoxy‐Breslow Intermediates

Umpolung N‐heterocyclic carbene (NHC) catalysis of non‐aldehyde substrates offers new pathways for C−C bond formation, but has proven challenging to develop in terms of viable substrate classes. Here, we demonstrate that pyridinium ions can undergo NHC addition and subsequent intramolecular C−C bond...

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Detalles Bibliográficos
Autores principales: Wu, Terence, Tatton, Matthew R., Greaney, Michael F.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2022
Materias:
Communications
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9306516/
https://www.ncbi.nlm.nih.gov/pubmed/35103381
http://dx.doi.org/10.1002/anie.202117524
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author Wu, Terence
Tatton, Matthew R.
Greaney, Michael F.
author_facet Wu, Terence
Tatton, Matthew R.
Greaney, Michael F.
author_sort Wu, Terence
collection PubMed
description Umpolung N‐heterocyclic carbene (NHC) catalysis of non‐aldehyde substrates offers new pathways for C−C bond formation, but has proven challenging to develop in terms of viable substrate classes. Here, we demonstrate that pyridinium ions can undergo NHC addition and subsequent intramolecular C−C bond formation through a deoxy‐Breslow intermediate. The alkylation demonstrates, for the first time, that deoxy‐Breslow intermediates are viable for catalytic umpolung of areniums.
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spelling pubmed-93065162022-07-28 NHC Catalysis for Umpolung Pyridinium Alkylation via Deoxy‐Breslow Intermediates Wu, Terence Tatton, Matthew R. Greaney, Michael F. Angew Chem Int Ed Engl Communications Umpolung N‐heterocyclic carbene (NHC) catalysis of non‐aldehyde substrates offers new pathways for C−C bond formation, but has proven challenging to develop in terms of viable substrate classes. Here, we demonstrate that pyridinium ions can undergo NHC addition and subsequent intramolecular C−C bond formation through a deoxy‐Breslow intermediate. The alkylation demonstrates, for the first time, that deoxy‐Breslow intermediates are viable for catalytic umpolung of areniums. John Wiley and Sons Inc. 2022-02-18 2022-04-04 /pmc/articles/PMC9306516/ /pubmed/35103381 http://dx.doi.org/10.1002/anie.202117524 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 Communications
Wu, Terence
Tatton, Matthew R.
Greaney, Michael F.
NHC Catalysis for Umpolung Pyridinium Alkylation via Deoxy‐Breslow Intermediates
title NHC Catalysis for Umpolung Pyridinium Alkylation via Deoxy‐Breslow Intermediates
title_full NHC Catalysis for Umpolung Pyridinium Alkylation via Deoxy‐Breslow Intermediates
title_fullStr NHC Catalysis for Umpolung Pyridinium Alkylation via Deoxy‐Breslow Intermediates
title_full_unstemmed NHC Catalysis for Umpolung Pyridinium Alkylation via Deoxy‐Breslow Intermediates
title_short NHC Catalysis for Umpolung Pyridinium Alkylation via Deoxy‐Breslow Intermediates
title_sort nhc catalysis for umpolung pyridinium alkylation via deoxy‐breslow intermediates
topic Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9306516/
https://www.ncbi.nlm.nih.gov/pubmed/35103381
http://dx.doi.org/10.1002/anie.202117524
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AT greaneymichaelf nhccatalysisforumpolungpyridiniumalkylationviadeoxybreslowintermediates

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