Solvent- and ligand-induced switch of selectivity in gold(I)-catalyzed tandem reactions of 3-propargylindoles

The selectivity of our previously described gold-catalyzed tandem reaction, 1,2-indole migration followed by aura-iso-Nazarov cyclization, of 3-propargylindoles bearing (hetero)aromatic substituents at both the propargylic and terminal positions, was reversed by the proper choice of the catalyst and...

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Autores principales: Álvarez, Estela, Miguel, Delia, García-García, Patricia, Fernández-Rodríguez, Manuel A, Rodríguez, Félix, Sanz, Roberto
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2011
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3135218/
https://www.ncbi.nlm.nih.gov/pubmed/21804873
http://dx.doi.org/10.3762/bjoc.7.89
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author Álvarez, Estela
Miguel, Delia
García-García, Patricia
Fernández-Rodríguez, Manuel A
Rodríguez, Félix
Sanz, Roberto
author_facet Álvarez, Estela
Miguel, Delia
García-García, Patricia
Fernández-Rodríguez, Manuel A
Rodríguez, Félix
Sanz, Roberto
author_sort Álvarez, Estela
collection PubMed
description The selectivity of our previously described gold-catalyzed tandem reaction, 1,2-indole migration followed by aura-iso-Nazarov cyclization, of 3-propargylindoles bearing (hetero)aromatic substituents at both the propargylic and terminal positions, was reversed by the proper choice of the catalyst and the reaction conditions. Thus, 3-(inden-2-yl)indoles, derived from an aura-Nazarov cyclization (instead of an aura-iso-Nazarov cyclization), were obtained in moderate to good yields from a variety of 3-propargylindoles.
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spelling pubmed-31352182011-07-29 Solvent- and ligand-induced switch of selectivity in gold(I)-catalyzed tandem reactions of 3-propargylindoles Álvarez, Estela Miguel, Delia García-García, Patricia Fernández-Rodríguez, Manuel A Rodríguez, Félix Sanz, Roberto Beilstein J Org Chem Full Research Paper The selectivity of our previously described gold-catalyzed tandem reaction, 1,2-indole migration followed by aura-iso-Nazarov cyclization, of 3-propargylindoles bearing (hetero)aromatic substituents at both the propargylic and terminal positions, was reversed by the proper choice of the catalyst and the reaction conditions. Thus, 3-(inden-2-yl)indoles, derived from an aura-Nazarov cyclization (instead of an aura-iso-Nazarov cyclization), were obtained in moderate to good yields from a variety of 3-propargylindoles. Beilstein-Institut 2011-06-09 /pmc/articles/PMC3135218/ /pubmed/21804873 http://dx.doi.org/10.3762/bjoc.7.89 Text en Copyright © 2011, Álvarez et al. https://creativecommons.org/licenses/by/2.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Full Research Paper
Álvarez, Estela
Miguel, Delia
García-García, Patricia
Fernández-Rodríguez, Manuel A
Rodríguez, Félix
Sanz, Roberto
Solvent- and ligand-induced switch of selectivity in gold(I)-catalyzed tandem reactions of 3-propargylindoles
title Solvent- and ligand-induced switch of selectivity in gold(I)-catalyzed tandem reactions of 3-propargylindoles
title_full Solvent- and ligand-induced switch of selectivity in gold(I)-catalyzed tandem reactions of 3-propargylindoles
title_fullStr Solvent- and ligand-induced switch of selectivity in gold(I)-catalyzed tandem reactions of 3-propargylindoles
title_full_unstemmed Solvent- and ligand-induced switch of selectivity in gold(I)-catalyzed tandem reactions of 3-propargylindoles
title_short Solvent- and ligand-induced switch of selectivity in gold(I)-catalyzed tandem reactions of 3-propargylindoles
title_sort solvent- and ligand-induced switch of selectivity in gold(i)-catalyzed tandem reactions of 3-propargylindoles
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3135218/
https://www.ncbi.nlm.nih.gov/pubmed/21804873
http://dx.doi.org/10.3762/bjoc.7.89
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