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

Autor: Estela Álvarez, Delia Miguel, Patricia García-García, Manuel A. Fernández-Rodríguez, Félix Rodríguez, Roberto Sanz
Jazyk: angličtina
Rok vydání: 2011
Předmět:
Zdroj: Beilstein Journal of Organic Chemistry, Vol 7, Iss 1, Pp 786-793 (2011)
Druh dokumentu: article
ISSN: 1860-5397
DOI: 10.3762/bjoc.7.89
Popis: 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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