Functionalization of Heterocyclic Cations

Tripp, Kyra

Student Work

Functionalization of Heterocyclic Cations

Pubblico Deposited

This work investigates the use of sulfoxonium ylides in ionic and photoredox reaction conditions, with the ultimate goal of the cyclopropanation of coumarins and chromenones. Sulfoxonium ylides are versatile compounds that can replace more dangerous diazo compounds in reactions such as insertions, [2+1] cycloadditions, and in heterocyclic motifs. Building on previous research, this work first explored the reactivity of coumarin benzopyrylium triflates with sulfoxonium ylides. However, it is more difficult to form benzopyrylium triflates from coumarin than from chromenones, likely due to the placement of the carbonyl group. Next, the work moved into the photoredox realm, experimenting with both coumarins and chromenones, and their reactivity with sulfoxonium ylides. This led to the discovery that neither heat nor light are necessary to form a chromenone benzopyrylium triflate, and that light changes this cyclopropanation reaction. This work also showed that while certain sulfoxonium ylides do form radical species under blue light, the radicals do not react with chromenones or chromenone benzopyrylium triflates under the tested conditions. Because of their ability to form radicals, sulfoxonium ylides hold promise in the area of photoredox chemistry.

This report represents the work of one or more WPI undergraduate students submitted to the faculty as evidence of completion of a degree requirement. WPI routinely publishes these reports on its website without editorial or peer review.

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