Novel copper-catalysed coupling reactions of diphenylmethane

Breski, A

Abstract

In this thesis, a novel synthesis of the drug fendiline was attempted. Fendiline was sold commercially as an angina therapeutic, and recent studies have shown that it is also anti-malarial and has activity against cancers with a high mortality rate. The novel synthesis attempted involved using lithiated diphenylmethane as the precursor to a Gilman reagent to perform a soft nucleophilic attack on N-α-phenylethyl aziridine. Upon carrying out this reaction, no desired product was formed, even with the addition of a Lewis acid. A review of the NMR spectra of the crude reaction mixture indicated that significant amounts of both diphenylpentane and tetraphenyl ethane were present as side products of the coupling reaction. After failing multiple attempts to synthesise fendiline using the proposed synthetic route, the focus of the project shifted to the research and development of hetero- and homo- cross-coupling reactions of the Gilman reagent. Different amounts of the reagents were used to find the ideal stoichiometric quantity, and results from the development only showed small amounts of the coupled products, diphenylpentane and tetraphenyl ethane were synthesised. It has been suggested that a way to improve the yield of this reaction might be to investigate analogues with stronger electron-withdrawing groups substituted on the aryl rings.

Citation

Breski, A. (in press). Novel copper-catalysed coupling reactions of diphenylmethane. (Dissertation). University of Salford

• Thesis Type: Dissertation
• Acceptance Date: Nov 23, 2021
• Deposit Date: Dec 14, 2021
• Publicly Available Date: Dec 14, 2021
• Award Date: Aug 13, 2021