Synthesis of Dihydroisobenzofurans via Palladium-Catalyzed Sequential Alkynylation/Annulation of 2-Bromobenzyl and 2-Chlorobenzyl Alcohols under Microwave Irradiation
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Título: | Synthesis of Dihydroisobenzofurans via Palladium-Catalyzed Sequential Alkynylation/Annulation of 2-Bromobenzyl and 2-Chlorobenzyl Alcohols under Microwave Irradiation |
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Autor/es: | Buxaderas Pérez de Armiñán, Eduardo | Alonso, Diego A. | Nájera, Carmen |
Grupo/s de investigación o GITE: | Síntesis Asimétrica (SINTAS) | Catálisis Estereoselectiva en Síntesis Orgánica (CESO) |
Centro, Departamento o Servicio: | Universidad de Alicante. Departamento de Química Orgánica | Universidad de Alicante. Instituto Universitario de Síntesis Orgánica |
Palabras clave: | Alkynes | Cycloisomerization | Dihydroisobenzofurans | Microwaves | Palladium | Sonogashira reaction |
Área/s de conocimiento: | Química Orgánica |
Fecha de publicación: | 3-nov-2014 |
Editor: | Wiley-VCH Verlag GmbH & Co. KGaA |
Cita bibliográfica: | Advanced Synthesis & Catalysis. 2014, 356(16): 3415-3421. doi:10.1002/adsc.201400457 |
Resumen: | The palladium-catalyzed synthesis of dihydroisobenzofurans has been performed by sequential Sonogashira cross-coupling/cyclization reactions between terminal alkynes and 2-(hydroxymethyl)bromo- and chlorobenzenes in methanol as solvent at 130 °C under microwave irradiation. A 4,4′-dichlorobenzophenone oxime-derived chloro-bridged palladacycle is an efficient pre-catalyst to perform this tandem process using 2-dicyclohexylphosphanyl-2′,4′,6′-triisopropylbiphenyl (Xphos) as ancillary ligand and potassium hydroxide as base in the absence of a copper cocatalyst. Under these conditions, functionalized 2-bromo- and 2-chlorobenzaldehydes are also suitable partners in the domino process affording phthalans in good yields. All the reactions can be performed under air and employing reagent-grade chemicals under low loading conditions (1 mol% Pd). |
Patrocinador/es: | Financial support from the MINECO (Project CTQ2010–20387), and Consolider INGENIO 2010 (CSD2007-00006), FEDER, from the Generalitat Valenciana (Project PROMETEO/2009/038), and the University of Alicante is acknowledged. |
URI: | http://hdl.handle.net/10045/46006 |
ISSN: | 1615-4150 (Print) | 1615-4169 (Online) |
DOI: | 10.1002/adsc.201400457 |
Idioma: | eng |
Tipo: | info:eu-repo/semantics/article |
Derechos: | © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim |
Revisión científica: | si |
Versión del editor: | http://dx.doi.org/10.1002/adsc.201400457 |
Aparece en las colecciones: | INV - SINTAS - Artículos de Revistas INV - CESO - Artículos de Revistas |
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2014_Buxaderas_etal_AS&C_final.pdf | Versión final (acceso restringido) | 418,44 kB | Adobe PDF | Abrir Solicitar una copia |
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