Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2013, Issue 8, Pages 1479-1484Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201201066
Keywords
Synthetic methods; Homogeneous catalysis; Palladium; Nitrogen heterocycles; Cross-coupling; Carbene ligands
Categories
Funding
- Spanish Ministerio de Ciencia e Innovacion (MICINN) [CTQ2007-65218, CTQ2011-24165]
- Consolider Ingenio [CSD2007-00006]
- Generalitat Valenciana [PROMETEO/2009/0349]
- Fondos Europeos para el Desarrollo Regional (FEDER)
- MICINN
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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 3(2) 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 degrees C under microwave irradiation during 60 min.
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