title: An Alternative to Precious Metals: Hg(ClO4)2·3H2O as a Cheap and Water-Tolerant Catalyst for the Cycloisomerization of Allenols.
abstract: Hg(ClO4)2·3H2O, a cheap, water-tolerant, and stable salt, catalyzes the cycloisomerization reaction or α-allenols to 2,5-dihydrofurans in an efficient and selective manner. The reaction is general and can be applied to differently functionalized substrates, including alkyl-substituted, aryl-substituted, enantiopure, and tertiary allenols. In addition, density functional theory (DFT) calculations were performed to obtain insight into various aspects of the controlled reactivity of α-allenols under mercury catalysis. They suggest a dual activation of the allenol by the Hg complex that drives the reaction to the chemoselective formation of 2,5-dihydrofurans.
authors.affiliation: †Grupo de Lactamas y Heterociclos Bioactivos, Departamento de Química Orgánica I, Unidad Asociada al CSIC, Facultad de Química, Universidad Complutense de Madrid, 28040 Madrid, Spain.
authors.forename: Benito
authors.initials: B
authors.lastname: Alcaide
authors.affiliation: ‡Instituto de Química Orgánica General, CSIC, Juan de la Cierva 3, 28006 Madrid, Spain.
authors.forename: Pedro
authors.initials: P
authors.lastname: Almendros
authors.affiliation: †Grupo de Lactamas y Heterociclos Bioactivos, Departamento de Química Orgánica I, Unidad Asociada al CSIC, Facultad de Química, Universidad Complutense de Madrid, 28040 Madrid, Spain.
authors.forename: Amparo
authors.initials: A
authors.lastname: Luna
authors.affiliation: ‡Instituto de Química Orgánica General, CSIC, Juan de la Cierva 3, 28006 Madrid, Spain.
authors.forename: Elena
authors.initials: E
authors.lastname: Soriano