Hiyama Cross-Coupling Using Palladium Nanoparticles

Significance

One-pot Hiyama cross-coupling of aryl halides 1 with phenyltrimethoxysilane (2) was achieved in water under fluoride-free conditions using palladium(0) nanoparticles which were prepared in situ from Na₂PdCl₄/SDS (sodium dodecyl sulfate). Thus, the reaction of aryl halides 1 with phenyltrimethoxysilane 2 was carried out with Na₂PdCl₄ and SDS in aqueous NaOH to give the corresponding biphenyls 3 in 86-96 yield (15 examples). The TEM (transmission electron microscope) observation and EDS (energy dispersive X-ray spectroscopy) analysis demonstrated the generation of Pd(0) nanoparticles (φ = 3-6 nm) during the reaction.