1,2-Functionalized Imidazoles as Palladium Ligands: An Efficient and Robust Catalytic System for the Fluorine-Free Hiyama Reaction

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Title: 1,2-Functionalized Imidazoles as Palladium Ligands: An Efficient and Robust Catalytic System for the Fluorine-Free Hiyama Reaction
Authors: Martínez Flores, Regina | 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 | Nitrogen heterocycles | Palladium | Ligand design | Cross-coupling
Knowledge Area: Química Orgánica
Issue Date: Feb-2014
Publisher: Wiley-VCH Verlag GmbH & Co. KGaA
Citation: European Journal of Organic Chemistry. 2014, 4: 872-877. doi:10.1002/ejoc.201301439
Abstract: A variety of hydroxy- and amino-functionalized imidazoles were prepared from 1-methyl- and 1-(diethoxymethyl)imidazole by means of isoprene-mediated lithiation followed by reaction with an electrophile. These compounds in combination with palladium acetate were screened as catalyst systems for the Hiyama reaction under fluorine-free conditions using microwave irradiation. The systematic study of the catalytic system showed 1-methyl-2-aminoalkylimidazole derivative L1 to be the best ligand, which was employed under solvent-free conditions with a 1:2 Pd/ligand ratio and TBAB (20 mol-%) as additive. The study has revealed an interaction between the Pd/ligand ratio and the amount of TBAB. The established catalytic system presented a certain degree of robustness, and it has been successfully employed in the coupling of a range of aryl bromides and chlorides with different aryl siloxanes. Furthermore, both reagents were employed in an equimolecular amount, without an excess of organosilane.
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/2009/039), from the Fondos Europeos para el Desarrollo Regional (FEDER) and from the Universidad de Alicante is acknowledged.
URI: http://hdl.handle.net/10045/46299
ISSN: 1434-193X (Print) | 1099-0690 (Online)
DOI: 10.1002/ejoc.201301439
Language: eng
Type: info:eu-repo/semantics/article
Rights: © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Peer Review: si
Publisher version: http://dx.doi.org/10.1002/ejoc.201301439
Appears in Collections:INV - SINTAS - Artículos de Revistas
INV - MATCAT - Artículos de Revistas
INV - AMIC - Artículos de Revistas

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