ABSTRACT
We exhibit for the first time to utilize the 1-butyl-3-methylimidazolium fluoride [bmim]F as an activator of the organosilanes with simple handling, storage, and work-up in contrast to traditional fluorine sources such as tetrabutylammonium fluoride (TBAF), which is requisite for Hiyama coupling. Palladium nanoparticles 2–5 nm in size stabilized in nitrile-functionalized 3-(3-cyanopropyl)-1-methyl-1H-imidazol-3-ium hexafluorophosphate {[CN-bmim]PF6} work as an in situ catalyst for carbon–carbon bond forming reactions of aromatic and heterocyclic halides with aryl- and vinyltrimethoxysilanes. A range of biphenyl derivatives, substituted styrenes, and aromatic heterocycles were obtained in 76–98% yield. Elevated yields of the cross-coupled products were obtained at a low catalyst loading of only 4 mol%, and the catalyst could be reused and recycled up to four times with only a slight loss in catalytic activity.
