Organic Chemistry

The 8th Annual Rhode Island Summer Undergraduate Research Fellows Conference

Gold-Catalyzed Phenylation of Heterocycles via C–H Bond Activation

Riley Davis¹, John Rhoat¹, Louis Marchetti¹, Brenton DeBoef^1
1 University of Rhode Island, Kingston, Rhode Island, United States

Abstract: This research aims for the regioselective, intermolecular addition of C-C bonds to heterocycles such as pyrroles, thiophenes, and furans, via C-H bond activation. Using a novel I(III) phenyl-source in the presence of a Au(I) catalyst results in a greener and more direct synthetic route for regioselectively accessing a variety of biarly compounds. This is exemplified by the successful synthesis of three heterocyclic biaryls. Further studies hope to increase yields, prove a wider scope of application, and elucidate the mechanism of this novel reaction.

Synthesis of Molecular Probe Biosensors for MRI and Treatments for Alzheimer’s Disease

John Rhoat¹, Brenton DeBoef^1
1 University of Rhode Island, Kingston, Rhode Island, United States

Abstract: A cyclotriveratrylene (CTV) compound has been identified as a novel molecular probe for ¹²⁹Xe magnetic resonance imaging (MRI) and spectroscopy. Past work in this field has relied on the use of Cryptophanes, cage shaped molecules whose syntheses are difficult and low yielding. CTV is a bowl-shaped compound that is also capable of reversibly binding xenon; this event can be detected in ¹²⁹Xe NMR spectrum. Due to the ease of synthesis of this novel CTV, we hypothesize that it can be a superior molecular probe for functionalization and eventual use as a targeted ¹²⁹Xe molecular probe.

PS48, (Z)-5-(4-chlorophenyl)-3-phenylpent-2-enoic acid, is known to bind phosphoinositide-dependent protein kinase 1 (PDK1a ) which is involved in insulin signaling pathways. The complete pathogenesis of Alzheimer’s disease (AD) is still unknown, but one emerging hypothesis is it may be a “type III diabetes,” due to the association of insulin depletion in the brain with early stages of AD.  Synthesis of PS48 has been achieved in our lab in 4 steps. We hope to use this compound as a key component in a collaborative effort towards the development of a library of novel kinase inhibitors for potential treatment of AD.