Synthesis of Dihydroisobenzofurans via Palladium-Catalyzed Sequential Alkynylation/Annulation of 2-Bromobenzyl and 2-Chlorobenzyl Alcohols under Microwave Irradiation
Contribuinte(s) |
Universidad de Alicante. Departamento de Química Orgánica Universidad de Alicante. Instituto Universitario de Síntesis Orgánica Síntesis Asimétrica (SINTAS) Catálisis Estereoselectiva en Síntesis Orgánica (CESO) |
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Data(s) |
23/03/2015
23/03/2015
03/11/2014
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Resumo |
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). 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. |
Identificador |
Advanced Synthesis & Catalysis. 2014, 356(16): 3415-3421. doi:10.1002/adsc.201400457 1615-4150 (Print) 1615-4169 (Online) http://hdl.handle.net/10045/46006 10.1002/adsc.201400457 |
Idioma(s) |
eng |
Publicador |
Wiley-VCH Verlag GmbH & Co. KGaA |
Relação |
http://dx.doi.org/10.1002/adsc.201400457 |
Direitos |
© 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim info:eu-repo/semantics/restrictedAccess |
Palavras-Chave | #Alkynes #Cycloisomerization #Dihydroisobenzofurans #Microwaves #Palladium #Sonogashira reaction #Química Orgánica |
Tipo |
info:eu-repo/semantics/article |