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
Títol: | 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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Autors: | Cano Monserrat, Rafael | Yus, Miguel | Ramón, Diego J. |
Grups d'investigació o GITE: | Nuevos Materiales y Catalizadores (MATCAT) | Síntesis Asimétrica (SINTAS) |
Centre, Departament o Servei: | Universidad de Alicante. Departamento de Química Orgánica | Universidad de Alicante. Instituto Universitario de Síntesis Orgánica |
Paraules clau: | Acid derivatives | Alkynes | Heterogeneous catalysis | Ketones | Magnetite | Iridium |
Àrees de coneixement: | Química Orgánica |
Data de publicació: | 26-d’agost-2013 |
Editor: | Elsevier |
Citació bibliogràfica: | Tetrahedron. 2013, 69(34): 7056-7065. doi:10.1016/j.tet.2013.06.041 |
Resum: | 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. |
Patrocinadors: | 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. |
URI: | http://hdl.handle.net/10045/40223 |
ISSN: | 0040-4020 (Print) | 1464-5416 (Online) |
DOI: | 10.1016/j.tet.2013.06.041 |
Idioma: | eng |
Tipus: | info:eu-repo/semantics/article |
Revisió científica: | si |
Versió de l'editor: | http://dx.doi.org/10.1016/j.tet.2013.06.041 |
Apareix a la col·lecció: | INV - SINTAS - Artículos de Revistas INV - MATCAT - Artículos de Revistas INV - AMIC - Artículos de Revistas |
Arxius per aquest ítem:
Arxiu | Descripció | Tamany | Format | |
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2013_Cano_etal_Tetrahedron_final.pdf | Versión final (acceso restringido) | 747,03 kB | Adobe PDF | Obrir Sol·licitar una còpia |
2013_Cano_etal_Tetrahedron.pdf | Accepted manuscript (acceso abierto) | 600,24 kB | Adobe PDF | Obrir Vista prèvia |
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