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Houk-Jung Organic Colloquium 247: Tianning Diao

Organic Colloquium

April 18, 2024 4:00 pm - 5:00 pm
Speaker Prof. Tianning Diao


Leveraging One- and Two-Electron Mechanisms in Nickel-Catalyzed Cross-Coupling

Abstract: While palladium-catalyzed cross-coupling reactions have revolutionized the construction of multi-aryl scaffolds in pharmaceutical synthesis, the reactivity of nickel in mediating radical pathways has expanded the scope of cross-coupling to include various alkyl motifs. Through our mechanistic investigations and an understanding of ligand effects, we established that strong -donor and -acceptor ligands, with redox activity, facilitate nickel catalysts to initiate radical formation, capture radicals, and direct bond formation from open-shell intermediates. Given the orthogonal reactivity of radicals with polar functional groups in biomolecules, these radical pathways have introduced innovative methods for synthesizing non-canonical peptides and carbohydrates, important for drug discovery. In contrast, two-electron pathways are crucial for nickel-catalyzed bi-aryl coupling. Building on this insight, we developed a novel ligand that enhances the reactivity of nickel-catalyzed Suzuki-Miyaura couplings, paving the way for the application of nickel catalysts in pharmaceutical process synthesis.

Diao Flyer

Prof. Tianning Diao

Organic Colloquium

Department of Chemistry

New York University