Cross-Coupling Reactions Catalyzed by Pd Nanoparticles
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One-Pot Hiyama–Heck Reaction Catalyzed by 1-Pd Nanoparticles
(Scheme 3): A screw-top sealable tube was charged with a magnetic
stir bar, 1-iodo-4-nitrobenzene (124.5 mg, 0.5 mmol), the corre-
sponding aryl iodide (0.25 mmol), triethoxy(vinyl)silane (210 μL,
1.0 mmol, 2 equiv.), NaOH (60 mg, 1.5 mmol), and 1-Pd NPs
(0.25 mol-% Pd). A mixture of methanol/water (1:1, 4 mL) was
added and the tube was sealed and heated to 100 °C for 48 h (TLC
and GC monitoring). The tube was then cooled to room tempera-
ture, the solvent was removed under vacuum and the residue was
purified by column chromatography (SiO2; hexane) to afford stil-
bene derivatives 45[23] (55 mg, 82%) and 46[24] (31 mg, 51%).
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Supporting Information (see footnote on the first page of this arti-
cle): Details of catalytic runs and characterization data of the corre-
sponding products.
Acknowledgments
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), Genera-
litat de Catalunya (project SGR2009-01441), Generalitat Valenci-
ana (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), Uni-
versidad de Alicante, for a grant.
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