LEAPS-MPS: Aryl Tosylates as Building Blocks for the Synthesis of Oxygen-containing Heterocycles

In this project managed by the Chemistry Division, Dr. Rashanique Quarels and her research team at Rowan University are developing photocatalytic conditions to generate cyclic compounds, heterocycles, and desulfonylation methods. A major focus of this project is conversion of phenols into value-added chemicals. The use of aryl tosylates, derived from phenols, as radical precursors is chosen due to the abundance of commercially available phenols, substrate stability, and utility. The goal of this research is to provide fundamental knowledge on visible-light-mediated, single-electron-transfer methods and resulting divergent mechanisms dependent upon photocatalyst selection. Another objective of this project is to implement several approaches to broaden participation and improve matriculation into the STEM workforce. This project will support: (1) the “Careers in STEM” seminar series, (2) the integration of research into the curriculum, and (3) research experiences for underrepresented students in chemistry and biochemistry. The Quarels research team will study organic and transition-metal catalysts that result in carbon-, oxygen-, and sulfur-centered radicals using aryl tosylates as radical precursors. Dr. Quarels and her research team will perform chemical synthesis, photoredox catalysis, NMR analysis, mass spectrometry analysis, and computational modeling studies. The overall work could provide a better understanding of the differences and complementarity between excited state organic and transition-metal photocatalysts. This award reflects NSF's statutory mission and has been deemed worthy of support through evaluation using the Foundation's intellectual merit and broader impacts review criteria.