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
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.
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.