Suzuki Coupling Catalyzed by (8-(dimesitylboryl)quinoline)palladium(0) Species: A Theoretical Analysis
Date of Award
Dr. Pere Miro
Dr. Bess Vlaisavljevich
Dr. Andreas Achazi
Computational Chemistry, Theoretical Analysis, Suzuki-Coupling, Oxidative Addition, Carbon-Fluorine bond
Inorganic Chemistry | Physical Chemistry
The Suzuki reaction is a catalyzed cross-coupling reaction which is of upmost importance in the formation of carbon-carbon (C-C) bonds in modern organic synthesis. Recently a new catalyst including an 8-(dimesitylboryl)quinoline for the coupling of aryl halides with phenylboronic acids was synthetized. We synthesized ligand that includes a frustrated Lewis pair, (quinolin-8-yl)dimesitylborane (DMBQ), complexed it with group X metals (nickel (Ni), palladium (Pd), and platinum (Pt)), and studied the process of oxidative addition with carbon-fluorine (C-F) bonds and activation towards Suzuki coupling. Mayer bond analysis and electron localization function maps showed a bond between the boron center in the ligand and the palladium center, but electron density, gradient and Laplacian maps showed no interaction. Thus, an elaborate extended transition state method involving natural chemical valence (ETS-NOCV) theory was performed to further characterize this interaction.
Rust, Haley S., "Suzuki Coupling Catalyzed by (8-(dimesitylboryl)quinoline)palladium(0) Species: A Theoretical Analysis" (2021). Honors Thesis. 155.