CCVC Seminar: Olivier Beaudoin - Direct vs. migratory Pd-catalyzed cross-coupling


Maass Chemistry Building Room 10, 801 rue Sherbrooke Ouest, Montreal, QC, H3A 0B8, CA

Our group's research is mainly focusing on the functionalization of unactivated C(sp3)-H bonds under
catalysis by palladium(0) complexes. A first strategy, which we have been pursuing for the past 15 years,
relies on intramolecular C-H activation and allows for the creation of a variety of interesting ring systems
from simple precursors.

More recently, we have investigated a different strategy for the intermolecular functionalization of remote
C(sp3)-H bonds via a Pd "chain-walk" mechanism. We showed that the site-selectivity of the cross-coupling
on the alkyl chain can be controlled by the ligand, with bulky phosphines giving rise to the direct coupling
product whereas homemade conformationally flexible ligands favor the migratory coupling product.

This lecture will present this concept in the context of two cross-couplings: the arylation of ester enolates
and the Negishi coupling.