Oxygen Activated, Palladium Nanoparticle Catalyzed, Ultrafast Cross-Coupling of Organolithium Reagents.
Dorus HeijnenFilippo TosiCarlos VilaMarc C A StuartPhilip H ElsingaWiktor SzymanskiBen L FeringaPublished in: Angewandte Chemie (International ed. in English) (2017)
The discovery of an ultrafast cross-coupling of alkyl- and aryllithium reagents with a range of aryl bromides is presented. The essential role of molecular oxygen to form the active palladium catalyst was established; palladium nanoparticles that are highly active in cross-coupling reactions with reaction times ranging from 5 s to 5 min are thus generated in situ. High selectivities were observed for a range of heterocycles and functional groups as well as for an expanded scope of organolithium reagents. The applicability of this method was showcased by the synthesis of the [11 C]-labeled PET tracer celecoxib.