Unveiling the Reactivity of Propargylic Hydroperoxides under Gold Catalysis.
Controlled gold-catalyzed reactions of primary and secondary propargylic hydroperoxides with a variety of nucleophiles including alcohols, phenols, 2-hydroxynaphthalene-1,4-dione, and indoles allow the direct and efficient synthesis of β-functionalized ketones. Moreover, the utility of some of the r...
| Publicado en: | Journal of the American Chemical Society Vol. 135; no. 2; pp. 898 - 906 |
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| Autores principales: | , , , , , |
| Formato: | Artículo |
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American Chemical Society
1/16/2013
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| Materias: | |
| Acceso en línea: | Ver este registro en EBSCOhost |
| fields | @attributes: recordID: 1 pdfLink: plink: https://search.ebscohost.com/login.aspx?direct=true&db=hlh&AN=85422777&site=ehost-live header: @attributes: shortDbName: hlh uiTerm: 85422777 longDbName: Humanities International Complete uiTag: AN controlInfo: bkinfo: jinfo: jid: 00027863 ACS jtl: Journal of the American Chemical Society issn: 00027863 maglogo: N pubinfo: dt: 1/16/2013 vid: 135 iid: 2 pid: 997 pub: American Chemical Society artinfo: ui: 85422777 10.1021/ja3108966 ppf: 898 ppct: 8 formats: tig: atl: Unveiling the Reactivity of Propargylic Hydroperoxides under Gold Catalysis. aug: au: Alcaide, Benito Almendros, Pedro Quirós, M. Teresa López, Ramón Menéndez, Maria I. Sochacka-Ćwiła, Aleksandra affil: Grupo de Lactamas y Heterociclos Bioactivos, Departamento de Química Orgârnca I, Unidad Asociada al CSIC, Facultad de Química, Universidad Complutense de Madrid, 28040-Madrid, Spain Instituto de Química Orgânica General, IQOG, CSIC, Juan de la Cierva 3, 28006-Madrid, Spain Departamento de Química Física y Analítica, Universidad de Oviedo, Julián Clavería 8, 33006 Oviedo, Asturias, Spain su: Gold catalyst activity Hydroperoxides Density functionals Ketones Nucleophilic addition (Chemistry) kinetics sug: subj: Gold catalyst activity Hydroperoxides Density functionals Ketones Nucleophilic addition (Chemistry) kinetics ab: Controlled gold-catalyzed reactions of primary and secondary propargylic hydroperoxides with a variety of nucleophiles including alcohols, phenols, 2-hydroxynaphthalene-1,4-dione, and indoles allow the direct and efficient synthesis of β-functionalized ketones. Moreover, the utility of some of the resulting products for the selective preparation of fused polycycles has been demonstrated. In addition, density functional theory (DFT) calculations and O-labeling experiments were performed to obtain an insight into various aspects of the controlled reactivity of propargylic hydroperoxides with external nucleophiles under gold catalysis. pubtype: Academic Journal doctype: Article src: R language: English refInfo: copyright: @attributes: flag: Y dt: @attributes: year: 2013 holdings: @attributes: islocal: N |
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