title: Brønsted Acid-Catalyzed Cascade Reactions Involving 1,2-Indole Migration.
abstract: A cascade reaction of indoles with propargylic diols involving an unprecedented metal-free 1,2-indole migration onto an alkyne was carried out. DFT calculations support a mechanism consisting of a concerted nucleophilic attack of the indole nucleus with loss of water, followed by the 1,2-migration and subsequent Nazarov cyclization. This Brønsted acid-catalyzed protocol affords indole-functionalized benzofulvene derivatives in high yields.
authors.affiliation: Área de Química Orgánica, Departamento de Química, Facultad de Ciencias, Universidad de Burgos, Pza. Misael Bañuelos s/n, 09001-Burgos (Spain).
authors.forename: Estela
authors.initials: E
authors.lastname: Álvarez
authors.affiliation: Departamento de Química Orgánica, Universidade de Vigo, Lagoas Marcosende, 36310-Vigo, Galicia (Spain).
authors.forename: Olalla
authors.initials: O
authors.lastname: Nieto Faza
authors.affiliation: Departamento de Química Orgánica, Universidade de Vigo, Lagoas Marcosende, 36310-Vigo, Galicia (Spain).
authors.forename: Carlos
authors.initials: C
authors.lastname: Silva López
authors.affiliation: Área de Química Orgánica, Departamento de Química, Facultad de Ciencias, Universidad de Burgos, Pza. Misael Bañuelos s/n, 09001-Burgos (Spain).
authors.forename: Manuel A
authors.initials: MA
authors.lastname: Fernández-Rodríguez
authors.affiliation: Área de Química Orgánica, Departamento de Química, Facultad de Ciencias, Universidad de Burgos, Pza. Misael Bañuelos s/n, 09001-Burgos (Spain). rsd@ubu.es.
authors.forename: Roberto
authors.initials: R
authors.lastname: Sanz
keywords: Brønsted acid; Nazarov cyclization; benzofulvenes; catalysis; indole migration