<br/>Hypervalent Iodine (HVI) compounds can be used to form carbon-carbon bonds and synthesize new pharmaceuticals. It has been observed that HVI compounds can produce molecules with T-shaped VSEPR geometries and dual benzene rings that engage in pi-stacking. The pi-stacking of HVI compounds has been theorized as the driving force of reactive intermediates that undergo Hypervalent Iodine Guided Electrophilic Substitution (HIGES). Based upon the proclivity of HVI compounds to form pi-stacking complexes, we seek to gain understanding of how the pi-stacking stabilizes the reactive intermediates and then use that knowledge to synthesize alkylated HVI compounds.<br/>Typically, alkylated HVI compounds are unstable and decompose but a few examples exist. Our research has discovered preliminary evidence that when hydrogen peroxide, acetic acid, and iodobenzene are reacted together, an alkylated HVI compound that is stabilized by pi-stacking is forming although the yields are low and isolation of the compound has proved difficult. The purpose of exploring alkylated HVI compounds is to extend HIGES methodology to sp3 carbon-carbon bond formation. The investigation of these pi-stacking compounds is warranted as the current experiment’s success could lead to the formation of a stable carbon-iodine bond, leading to never before seen possibilities in the pharmaceutical industry.

Pi-stacking complexes in hypervalent iodine chemistry

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