An NHC-Catalyzed Desulfonylative Smiles Rearrangement of Pyrrole and Indole Carboxaldehydes

[Image: see text] The use of catalysis methods to enable Smiles rearrangement opens up new substrate classes for arylation under mild conditions. Here, we describe an N-heterocyclic carbene (NHC) catalysis system that accesses indole and pyrrole aldehyde substrates in a desulfonylative Smiles proces...

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Autores principales: Swaby, Caitlin, Taylor, Alfie, Greaney, Michael F.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2023
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10476196/
https://www.ncbi.nlm.nih.gov/pubmed/37589318
http://dx.doi.org/10.1021/acs.joc.3c01089
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author Swaby, Caitlin
Taylor, Alfie
Greaney, Michael F.
author_facet Swaby, Caitlin
Taylor, Alfie
Greaney, Michael F.
author_sort Swaby, Caitlin
collection PubMed
description [Image: see text] The use of catalysis methods to enable Smiles rearrangement opens up new substrate classes for arylation under mild conditions. Here, we describe an N-heterocyclic carbene (NHC) catalysis system that accesses indole and pyrrole aldehyde substrates in a desulfonylative Smiles process. The reaction proceeds under mild, transition-metal-free conditions and captures acyl anion reactivity for the synthesis of a diverse array of 2-aroyl indoles and pyrroles from readily available sulfonamide starting materials.
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spelling pubmed-104761962023-09-05 An NHC-Catalyzed Desulfonylative Smiles Rearrangement of Pyrrole and Indole Carboxaldehydes Swaby, Caitlin Taylor, Alfie Greaney, Michael F. J Org Chem [Image: see text] The use of catalysis methods to enable Smiles rearrangement opens up new substrate classes for arylation under mild conditions. Here, we describe an N-heterocyclic carbene (NHC) catalysis system that accesses indole and pyrrole aldehyde substrates in a desulfonylative Smiles process. The reaction proceeds under mild, transition-metal-free conditions and captures acyl anion reactivity for the synthesis of a diverse array of 2-aroyl indoles and pyrroles from readily available sulfonamide starting materials. American Chemical Society 2023-08-17 /pmc/articles/PMC10476196/ /pubmed/37589318 http://dx.doi.org/10.1021/acs.joc.3c01089 Text en © 2023 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Swaby, Caitlin
Taylor, Alfie
Greaney, Michael F.
An NHC-Catalyzed Desulfonylative Smiles Rearrangement of Pyrrole and Indole Carboxaldehydes
title An NHC-Catalyzed Desulfonylative Smiles Rearrangement of Pyrrole and Indole Carboxaldehydes
title_full An NHC-Catalyzed Desulfonylative Smiles Rearrangement of Pyrrole and Indole Carboxaldehydes
title_fullStr An NHC-Catalyzed Desulfonylative Smiles Rearrangement of Pyrrole and Indole Carboxaldehydes
title_full_unstemmed An NHC-Catalyzed Desulfonylative Smiles Rearrangement of Pyrrole and Indole Carboxaldehydes
title_short An NHC-Catalyzed Desulfonylative Smiles Rearrangement of Pyrrole and Indole Carboxaldehydes
title_sort nhc-catalyzed desulfonylative smiles rearrangement of pyrrole and indole carboxaldehydes
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10476196/
https://www.ncbi.nlm.nih.gov/pubmed/37589318
http://dx.doi.org/10.1021/acs.joc.3c01089
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