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UBC Theses and Dissertations

Extending the boundaries of diaryliodonium reagents : expressing I-nucleophilicity of aryl iodides and metal-free preparation of sulfonium salts Racicot, Léanne


Diaryliodonium salts are a well-established class of hypervalent iodine reagents and act as aryl group transfer agents towards nucleophiles. This work established the possibility of metathesis between diaryliodonium triflates and various iodoarenes. In an effort to further understand the factors that govern this process, λ³-iodanes containing 2-thienyl moieties were prepared. As a result, aryl iodides unable to undergo metatesis previously were found to be suitable nucleophiles as the metathesis favors diaryliodonium species where more nucleofugal aryl iodides, such as 2-iodothiophene, are expelled during the course of the reaction. In addition, we showed that copper catalysis was not necessary for the arylation of sulfides, selenides and tellurides. Indeed, thermal reactions between the chalcogenides and diaryliodonium triflates afforded the corresponding triarylchalcogenium salts in good yields. This is particularly significant for the preparation of the triaryltelluronium species, as only limited protocols for their preparation were known.

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