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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| Format: | Article |
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Beilstein-Institut
2011-06-01
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| Series: | Beilstein Journal of Organic Chemistry |
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| Online Access: | https://doi.org/10.3762/bjoc.7.89 |
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| author | Estela Álvarez Delia Miguel Patricia García-García Manuel A. Fernández-Rodríguez Félix Rodríguez Roberto Sanz |
| author_facet | Estela Álvarez Delia Miguel Patricia García-García Manuel A. Fernández-Rodríguez Félix Rodríguez Roberto Sanz |
| author_sort | Estela Álvarez |
| collection | DOAJ |
| 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. |
| first_indexed | 2024-12-13T23:17:36Z |
| format | Article |
| id | doaj.art-282d09694b2f4fe1b5ad2a177641ca58 |
| institution | Directory Open Access Journal |
| issn | 1860-5397 |
| language | English |
| last_indexed | 2024-12-13T23:17:36Z |
| publishDate | 2011-06-01 |
| publisher | Beilstein-Institut |
| record_format | Article |
| series | Beilstein Journal of Organic Chemistry |
| spelling | doaj.art-282d09694b2f4fe1b5ad2a177641ca582022-12-21T23:27:53ZengBeilstein-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 |
| 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 |
| 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 | catalysis gold indoles Nazarov cyclizations selectivity |
| url | https://doi.org/10.3762/bjoc.7.89 |
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