Your browser doesn't support javascript.
loading
Metal-Catalyzed Cyclization Reactions of 2,3,4-Trien-1-ols: A Joint Experimental-Computational Study.
Alcaide, Benito; Almendros, Pedro; Cembellín, Sara; Fernández, Israel; Martínez Del Campo, Teresa.
Afiliación
  • Alcaide B; 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. alcaideb@quim.ucm.es.
  • Almendros P; Instituto de Qímica General, Consejo Superior de Investigaciones Científicas, IQOG-CSIC, Juan de la Cierva 3, 28006, Madrid, Spain. Palmendros@iqog.csic.es.
  • Cembellín S; 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.
  • Fernández I; Departamento de Química Orgánica I, Facultad de Química, Universidad Complutense de Madrid, 28040, Madrid, Spain. israel@quim.ucm.es.
  • Martínez Del Campo T; 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.
Chemistry ; 22(33): 11667-76, 2016 Aug 08.
Article en En | MEDLINE | ID: mdl-27383332
Controlled preparation of tri- and tetrasubstituted furans, as well as carbazoles has been achieved through chemo- and regioselective metal-catalyzed cyclization reactions of cumulenic alcohols. The gold- and palladium-catalyzed cycloisomerization reactions of cumulenols, including indole-tethered 2,3,4-trien-1-ols, to trisubstituted furans was effective, due to a 5-endo-dig oxycyclization by attack of the hydroxy group onto the central cumulene double bond. In contrast, palladium-catalyzed heterocyclization/coupling reactions with 3-bromoprop-1-enes furnished tetrasubstituted furans. Also studied was the palladium-catalyzed cyclization/coupling sequence involving protected indole-tethered 2,3,4-trien-1-ols and 3-bromoprop-1-enes that exclusively generated trisubstituted carbazole derivatives. These results could be explained through a selective 6-endo-dig cumulenic hydroarylation, followed by aromatization. DFT calculations were carried out to understand this difference in reactivity.
Palabras clave

Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Idioma: En Revista: Chemistry Asunto de la revista: QUIMICA Año: 2016 Tipo del documento: Article País de afiliación: España Pais de publicación: Alemania

Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Idioma: En Revista: Chemistry Asunto de la revista: QUIMICA Año: 2016 Tipo del documento: Article País de afiliación: España Pais de publicación: Alemania