Mild Ligand-Directed Pd-Catalyzed C–H Arylation and Alkylation

Seminar series
Organic Colloquium
Mon, May 20 5:00pm
Cram Conference Room – 3440 Mol Sci
Speaker Dr. Sharon R. Neufeldt
California Institute of Technology
Division of Chemistry and Chemical Engineering

Special Organic Seminar

"Mild Ligand-Directed Pd-Catalyzed C–H Arylation and Alkylation"

Abstract.  Transition metal catalysis can enable typically inert C–H bonds to undergo functionalization via a metal-catalyzed C–H activation step.  In particular, Pd-catalyzed ligand-directed C–H functionalization reactions have emerged as powerful methods for diverse bond constructions.  Nevertheless, the applicability of these methodologies is often restricted by harsh reaction conditions and limited generality.  This seminar describes recent efforts to address these challenges by accessing alternative mechanistic paradigms using high-valent Pd catalysis.  Toward this end, we have developed a room-temperature C–H arylation methodology by rerouting the mechanism of Pd-catalyzed C–H arylation with diaryliodonium salts from an ionic pathway through a radical-mediated pathway.  A mild C–H alkylation reaction using potassium alkyltrifluoroborates in conjunction with MnF3 is additionally described.