NHC-Ligand Effectiveness in the Fluorine-Free Hiyama Reaction of Aryl Halides

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Title: NHC-Ligand Effectiveness in the Fluorine-Free Hiyama Reaction of Aryl Halides
Authors: Peñafiel Andrés, Itziar | Pastor, Isidro M. | Yus, Miguel
Research Group/s: Nuevos Materiales y Catalizadores (MATCAT) | Síntesis Asimétrica (SINTAS)
Center, Department or Service: Universidad de Alicante. Departamento de Química Orgánica | Universidad de Alicante. Instituto Universitario de Síntesis Orgánica
Keywords: Synthetic methods | Homogeneous catalysis | Palladium | Nitrogen heterocycles | Cross-coupling | Carbene li­gands
Knowledge Area: Química Orgánica
Issue Date: Mar-2013
Publisher: Wiley-VCH Verlag GmbH & Co. KGaA
Citation: European Journal of Organic Chemistry. 2013, 2013(8): 1479-1484. doi:10.1002/ejoc.201201066
Abstract: 1-Benzyl-3-(2-hydroxy-2-phenylethyl)imidazolium chloride (5), which is a precursor of an N-heterocyclic carbene ligand, in combination with palladium acetate, has been employed as an effective catalyst for the fluorine-free Hiyama reaction. A systematic study of the catalytic mixture, by a 32 factorial design, has revealed that both the amount of palladium and the Pd/NHC precursor ratio are important factors for obtaining good yields of the coupling products, indicating an interaction between them. The best catalytic system involves mixing 0.1 mol-% palladium acetate in a 1:5 ratio (Pd/salt 5), which allows the effective coupling of a range of aryl bromides and chlorides with trimethoxy(phenyl)silane. The Hiyama reactions are carried out in NaOH solution (50 % H2O w/w), at 120 °C under microwave irradiation during 60 min.
Sponsor: Financial support from the Spanish Ministerio de Ciencia e Innovación (MICINN) (project numbers CTQ2007-65218, CTQ2011-24165), from Consolider Ingenio 2010 (CSD2007-00006), from the Generalitat Valenciana (PROMETEO/2009/0349), and from the Fondos Europeos para el Desarrollo Regional (FEDER) is acknowledged. I. P. thanks the MICINN for a predoctoral fellowship.
URI: http://hdl.handle.net/10045/40222
ISSN: 1434-193X (Print) | 1099-0690 (Online)
DOI: 10.1002/ejoc.201201066
Language: eng
Type: info:eu-repo/semantics/article
Rights: © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Peer Review: si
Publisher version: http://dx.doi.org/10.1002/ejoc.201201066
Appears in Collections:INV - SINTAS - Artículos de Revistas
INV - MATCAT - Artículos de Revistas
INV - AMIC - Artículos de Revistas

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