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Ligand-free copper catalysed cross-coupling of sulfonamides with aryl halides
Author
Low, Nigel Ping Soon
Supervisor
Teo, Yong Chua
Abstract
This study aims to fill in a gap in our collective knowledge regarding the use of Cu2O as a copper catalyst precursor for Ullmann-type cross-coupling reactions; in particular, for N-arylation of sulfonamides with aryl halides. Reported herein are the results of optimisation studies and substrate studies for both reactants. During the optimisation, it was found that polar aprotic solvents, bases having large cations with a dispersed charge, and copper salts, all contributed to the high yields of the reaction. Subsequently, factors affecting the reaction, such as the electronic and steric environments, were investigated using a selection of substituted aryl halides. In general, it was found that reaction with electron-withdrawing groups on the aryl halide were controlled by steric factors, while reaction with electron-donating groups on the aryl halide were more controlled by electronic factors. Finally, a reaction mechanism via π-complexation with the Cu catalyst is proposed.
Date Issued
2021
Call Number
QD181.C9 Low
Date Submitted
2021