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Sulfoxide Directed Metal-free Cross Coupling: Propargylation of Aromatic and Heteroaromatic Systems

Zhang, Yuntong

[Thesis]. Manchester, UK: The University of Manchester; 2015.

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Abstract

This thesis describes the development of an interrupted Pummerer reaction and its application in aromatic and hereroaromatic carbon-hydrogen substitution. During the development of the approach, a wide range of aryl and heteroaryl sulfoxides has been synthesised in order to investigate the scope of ortho-propargylation. Good to excellent yields of propargyl aromatic and heteroaromatic products have been obtained. Moreover, propargylated substrates can be treated with iodine undergoing 5-exo-dig cyclisation leading to benzothiophenes and thienylthiophenes, which have industrially-significant applications in organic materials, pharmaceuticals and chemosensors. Under different conditions, different functionalised benzothiophenes can be obtained. Further extending this reaction in two directional cyclisation of propargyl naphthalene sulfides gives napthodithiophenes motif found in organic materials.