Nickel-Catalyzed ?-Arylation of Secondary Amides

Within the realm of transition metal-catalyzed reactions, considerable interest lies in the ability to generate carbon-carbon linkages using cheap and abundant catalysts and reagents, as products derived from these couplings are widespread amongst bioactive molecules including pharmaceutical and agricultural agents. The importance of catalyst design in facilitating particularly challenging couplings of this type cannot be overstated, as even small perturbations in reaction conditions can have profound effects on the governed catalytic performance and selectivity. In this project, we seek to utilize Earth-abundant Nickel-based catalyst optimization to perform the alpha-arylation (alpha to carbonyl-carbon) of secondary amides with heteroaryl pseudohalide electrophiles. Success in the proposed research is likely to be broadly impactful in terms of the improved conceptual understanding of Ni catalysis in terms of potential applications in both the pharmaceutical and agricultural industries. In particular, the proposed methodologies involve use of more sustainable Ni catalysts (vs. Pd) for converting inexpensive and abundant reagents into useful bioactive molecules.

Faculty Supervisor:

Mark Stradiotto

Student:

Partner:

Institute of Chemical Research of Catalonia

Discipline:

Physics

Sector:

Pharmaceuticals; Sustainability & the Environment

University:

Dalhousie University

Program: