Heck, Sonogashira, and Hiyama Reactions Catalyzed by Palladium Nanoparticles Stabilized by Tris-Imidazolium Salt

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Title: Heck, Sonogashira, and Hiyama Reactions Catalyzed by Palladium Nanoparticles Stabilized by Tris-Imidazolium Salt
Authors: Planellas, Marc | Moglie, Yanina | Alonso, Francisco | Yus, Miguel | Pleixats, Roser | Shafir, Alexandr
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: Heterogeneous catalysis | Nanoparticles | Palladium | Cross-coupling
Knowledge Area: Química Orgánica
Issue Date: May-2014
Publisher: Wiley-VCH Verlag GmbH & Co. KGaA
Citation: European Journal of Organic Chemistry. 2014, 14: 3001-3008. doi:10.1002/ejoc.201400162
Abstract: Palladium nanoparticles, prepared by the hydrogenation of Pd(dba)2 in the presence of a tris-imidazolium iodide as stabilizer, act as an efficient catalyst for Heck and copper-free Sonogashira reactions with a range of aryl iodides and bromides at 0.2 mol-% Pd loading. Moreover, we describe a convenient protocol for the fluoride-free Hiyama coupling of vinylsilanes with aryl iodides that involves the use of sodium hydroxide as promoter in a methanol/water mixture. Under the developed conditions, one-pot, double Heck and Hiyama–Heck reactions are successfully achieved.
Sponsor: The authors acknowledge financial support from Ministerio de Ciencia e Innovación (MICINN) of Spain (project numbers CTQ2007-65218, CTQ2009-07881/BQU and CTQ2011-24151/BQU), Consolider Ingenio 2010 (project CSD2007-00006), Generalitat de Catalunya (project SGR2009-01441), Generalitat Valenciana (PROMETEO/2009/039) and Fondo Europeo de Desarrollo Regional (FEDER). A. S. was supported through a Ramón y Cajal contract from the Spanish Ministerio de Educación y Ciencia (MEC); Y. M. thanks the Instituto de Síntesis Orgánica (ISO), Universidad de Alicante, for a grant.
URI: http://hdl.handle.net/10045/46304
ISSN: 1434-193X (Print) | 1099-0690 (Online)
DOI: 10.1002/ejoc.201400162
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.201400162
Appears in Collections:INV - SINTAS - Artículos de Revistas
INV - MATCAT - Artículos de Revistas

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