Photoredox catalysis (PRC) provides efficient access of highly substituted cyclobutane rings via [2+2] photocycloadditions. Substituted cyclobutanes are a prevalent structural motif of many biological active natural products; they often exhibit antiviral, anticancer, or antifungal related properties. We have initiated studies to explore and expand the scope and limitations of Ruthenium PRC as a means to access cyclobutanes containing substituents arising from substituted 1,2-dihydronaphthalene or indene precursors. Building on the work of Chen et al., Ru(bpy)32+ and Ru(bpm)32+ will be initially screened against a small library of olefins, which can be synthesized in two steps from a variety of commercially available tetralones or 1-indanones. The library will be partially produced by an upper-level advanced organic chemistry laboratory class utilizing a Course-Based Undergraduate Research (CURE) process to produce starting material olefins and preliminary catalysis data.

Synthesis of 1,2-dihydronaphthalenes and indenes for substrate scope and limitation studies of substituted cyclobutane formation via photoredox catalysis

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.