Catalyzed addition of acid chlorides to alkynes by unmodified nano-powder magnetite: synthesis of chlorovinyl ketones, furans, and related cyclopentenone derivatives
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http://hdl.handle.net/10045/40223
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Campo DC | Valor | Idioma |
---|---|---|
dc.contributor | Nuevos Materiales y Catalizadores (MATCAT) | es |
dc.contributor | Síntesis Asimétrica (SINTAS) | es |
dc.contributor.author | Cano Monserrat, Rafael | - |
dc.contributor.author | Yus, Miguel | - |
dc.contributor.author | Ramón, Diego J. | - |
dc.contributor.other | Universidad de Alicante. Departamento de Química Orgánica | es |
dc.contributor.other | Universidad de Alicante. Instituto Universitario de Síntesis Orgánica | es |
dc.date.accessioned | 2014-09-12T08:35:09Z | - |
dc.date.available | 2014-09-12T08:35:09Z | - |
dc.date.issued | 2013-08-26 | - |
dc.identifier.citation | Tetrahedron. 2013, 69(34): 7056-7065. doi:10.1016/j.tet.2013.06.041 | es |
dc.identifier.issn | 0040-4020 (Print) | - |
dc.identifier.issn | 1464-5416 (Online) | - |
dc.identifier.uri | http://hdl.handle.net/10045/40223 | - |
dc.description.abstract | Inexpensive and commercially available nano-powder magnetite is an excellent catalyst for the addition of acid chlorides to internal and terminal alkynes, yielding the corresponding chlorovinyl ketones in good yields. The process has been applied to the synthesis of 5-chloro-4-arylcyclopent-2-enones, 3-aryl-1H-cyclopenta[a]naphthalen-1-ones, and (E)-3-alkylidene-2,3-dihydro-1H-cyclopenta[a]naphthalen-1-ones, just by changing the nature of the starting acid chloride or the alkyne. All tested processes elapse with an acceptable or excellent regio- and stereo-selectivity. Moreover, the use of the iridium impregnated on magnetite catalyst permits the integration of the chloroacylation process with a second dehydrochlorination–annulation process to yield, in one-pot, 1-aryl-2,4-dialkylfurans in good yields, independently of the nature of the starting reagents, and including the heteroaromatic ones. | es |
dc.description.sponsorship | This work was supported by the current Spanish Ministerio de Economía y Competitividad (Consolider Ingenio 2010 CSD2007-00006 and CTQ2011-24151) and the Generalitat Valenciana (G.V.; PROMETEO 2009/03, FEDER). R.C. thanks to G.V. for a fellowship through the PROMETEO program. | es |
dc.language | eng | es |
dc.publisher | Elsevier | es |
dc.subject | Acid derivatives | es |
dc.subject | Alkynes | es |
dc.subject | Heterogeneous catalysis | es |
dc.subject | Ketones | es |
dc.subject | Magnetite | es |
dc.subject | Iridium | es |
dc.subject.other | Química Orgánica | es |
dc.title | Catalyzed addition of acid chlorides to alkynes by unmodified nano-powder magnetite: synthesis of chlorovinyl ketones, furans, and related cyclopentenone derivatives | es |
dc.type | info:eu-repo/semantics/article | es |
dc.peerreviewed | si | es |
dc.identifier.doi | 10.1016/j.tet.2013.06.041 | - |
dc.relation.publisherversion | http://dx.doi.org/10.1016/j.tet.2013.06.041 | es |
dc.rights.accessRights | info:eu-repo/semantics/openAccess | es |
Aparece en las colecciones: | INV - SINTAS - Artículos de Revistas INV - MATCAT - Artículos de Revistas INV - AMIC - Artículos de Revistas |
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2013_Cano_etal_Tetrahedron_final.pdf | Versión final (acceso restringido) | 747,03 kB | Adobe PDF | Abrir Solicitar una copia |
2013_Cano_etal_Tetrahedron.pdf | Accepted manuscript (acceso abierto) | 600,24 kB | Adobe PDF | Abrir Vista previa |
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