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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Main Authors:	Estela Álvarez, Delia Miguel, Patricia García-García, Manuel A. Fernández-Rodríguez, Félix Rodríguez, Roberto Sanz
Format:	Article
Language:	English
Published:	Beilstein-Institut 2011-06-01
Series:	Beilstein Journal of Organic Chemistry
Subjects:	catalysis gold indoles Nazarov cyclizations selectivity
Online Access:	https://doi.org/10.3762/bjoc.7.89

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spelling	doaj-282d09694b2f4fe1b5ad2a177641ca582021-02-02T00:48:34ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972011-06-017178679310.3762/bjoc.7.891860-5397-7-89Solvent- and ligand-induced switch of selectivity in gold(I)-catalyzed tandem reactions of 3-propargylindolesEstela Álvarez0Delia Miguel1Patricia García-García2Manuel A. Fernández-Rodríguez3Félix Rodríguez4Roberto Sanz5Área de Química Orgánica, Departamento de Química, Facultad de Ciencias, Universidad de Burgos, Pza. Misael Bañuelos s/n, 09001 Burgos, SpainÁrea de Química Orgánica, Departamento de Química, Facultad de Ciencias, Universidad de Burgos, Pza. Misael Bañuelos s/n, 09001 Burgos, SpainÁrea de Química Orgánica, Departamento de Química, Facultad de Ciencias, Universidad de Burgos, Pza. Misael Bañuelos s/n, 09001 Burgos, SpainÁrea de Química Orgánica, Departamento de Química, Facultad de Ciencias, Universidad de Burgos, Pza. Misael Bañuelos s/n, 09001 Burgos, SpainInstituto Universitario de Química Organometálica “Enrique Moles”, Universidad de Oviedo, C/Julián Clavería 8, 33006 Oviedo, SpainÁrea de Química Orgánica, Departamento de Química, Facultad de Ciencias, Universidad de Burgos, Pza. Misael Bañuelos s/n, 09001 Burgos, SpainThe 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.https://doi.org/10.3762/bjoc.7.89catalysisgoldindolesNazarov cyclizationsselectivity
collection	DOAJ
language	English
format	Article
sources	DOAJ
author	Estela Álvarez Delia Miguel Patricia García-García Manuel A. Fernández-Rodríguez Félix Rodríguez Roberto Sanz
spellingShingle	Estela Álvarez Delia Miguel Patricia García-García Manuel A. Fernández-Rodríguez Félix Rodríguez Roberto Sanz Solvent- and ligand-induced switch of selectivity in gold(I)-catalyzed tandem reactions of 3-propargylindoles Beilstein Journal of Organic Chemistry catalysis gold indoles Nazarov cyclizations selectivity
author_facet	Estela Álvarez Delia Miguel Patricia García-García Manuel A. Fernández-Rodríguez Félix Rodríguez Roberto Sanz
author_sort	Estela Álvarez
title	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_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_sort	solvent- and ligand-induced switch of selectivity in gold(i)-catalyzed tandem reactions of 3-propargylindoles
publisher	Beilstein-Institut
series	Beilstein Journal of Organic Chemistry
issn	1860-5397
publishDate	2011-06-01
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.
topic	catalysis gold indoles Nazarov cyclizations selectivity
url	https://doi.org/10.3762/bjoc.7.89
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Solvent- and ligand-induced switch of selectivity in gold(I)-catalyzed tandem reactions of 3-propargylindoles

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