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An Alternative to Precious Metals: Hg(ClO<inf>4</inf>)<inf>2</inf>·3H<inf>2</inf>O as a Cheap and Water-Tolerant Catalyst for the Cycloisomerization of Allenols

AutorAlcaide, Benito ; Almendros, Pedro ; Luna, Amparo; Soriano, Elena
Fecha de publicación2015
EditorAmerican Chemical Society
CitaciónJournal of Organic Chemistry 80: 7050-7057 (2015)
ResumenHg(ClO<inf>4</inf>)<inf>2</inf>·3H<inf>2</inf>O, 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.
Versión del editorhttp://dx.doi.org/10.1021/acs.joc.5b00887
URIhttp://hdl.handle.net/10261/125546
DOI10.1021/acs.joc.5b00887
Identificadoresdoi: 10.1021/acs.joc.5b00887
issn: 1520-6904
e-issn: 1520-6904
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