Computational Investigation of Substrate Dependence of the Suzuki Coupling Reaction in Medicinal Chemistry

Author(s): Karan Kalia, Michelle De Angelis, and Hannah Bethman. Faculty Mentor: Daniel Lambrecht. Institution: Florida Gulf Coast University Address:10501 FGCU Blvd S, Fort Myers, FL 33965

The Suzuki-Miyaura coupling is the most widely used carbon-carbon coupling reaction in medicinal chemistry. Palladium with nitrogen-heterocyclic carbene ligands of type IPr=N,N‘-bis(2,6-diisopropylphenyl)imidazol-2-ylidene has been shown to be an efficient catalyst for aryl-aryl couplings, giving access to the biaryl functionality frequently found in contemporary drug molecules. However, previous studies focused on model substrates, leaving unanswered the question of whether the catalyst would also perform well on other types of substrates. This work uses computation to study the substrate dependence of the activation energy to assess for which types of substrates the catalyst would be active. Our hypothesis was that electron-donating substituents would lower the activation barrier. To test this hypothesis, substrates were modified with electron-donating groups NH2, OMe, and OH, and electron-withdrawing groups NO2 and CF3. Activation barriers were then predicted using computational approaches.

Additional Abstract Information

Presenters: Karan Kalia, Hannah Bethman, Michelle De Angelis

Institution: Florida Gulf Coast University

Type: Poster

Subject: Biochemistry

Status: Approved

Time and Location

Session: Poster 1
Date/Time: Mon 1:30pm-2:30pm
Session Number: 2160