Palladium Catalysis

Cross-Coupling Reactions





We reported various palladium-catalyzed procedures to perform the cross-coupling between triarylbismuths, trialkylbismuths and tricyclopropylbismuth and aryl or heteroarylhalides and triflates. These reactions operate under simple conditions and use

commercially available catalysts. We

demonstrated that lithium and rubidium

salts improve the efficience of those

reactions. Our group also demonstrated

that contrary to many R–M species,

trialkylbismuth species are not proned

to Beta-hydride elimination side

reactions. Our methods show excellent

functional group tolerance and allow

the transfer of aryl, alkyl and cyclopropyl

groups on scaffolds that are commonly

used in medicinal chemistry.

couplage palladium.tiff
Coupage carbonylatif.tiff

Our group also developed methods for the carbonylative cross-coupling reaction involving triarylbismuths that operate using a commercial palladium catalayst, that is, tetrakis(triphenylphosphine)palladium, and that function under mild conditions. We reported the first carbonylative cross-coupling reaction that involves a cyclopropyl-donor reagent and that leads to aryl-cyclopropylketones. This carbonylative cross-coupling reaction involves tricyclopropylbismuth as the cyclopropylating reagent and is catalyzed by an NHC-allyl palladium chloride complex.