CONTACT
4201 Henry Avenue
Hayward Hall, Room 220B
Philadelphia, PA 19144
Our group focuses on developing new reagents and strategies for organic synthesis and applying them in the synthesis of medicinally interesting targets. Specific ongoing projects within this theme include: 1) the development of bifunctional reagents to synthesize heterocycles using photoredox catalysis, 2) the deployment of Bobbitt's salt as a sustainable oxidant for chemoselective oxidations, and 3) collaborative studies on the use of fluorine-containing isosteres in phenolic natural products.
Research Projects
Blue LED-driven methods for heterocycle synthesis
Heterocycles are widespread among molecules of biological relevance. Numerous methods to construct saturated heterocycles exist, but few operate under highly mild conditions and tolerate various substituents with unprotected functional groups. Our group is involved in developing bifunctional reagents that are capable of heterocycle synthesis through a one-pot sequence of blue LED-enabled cross-coupling and polar substitution.
Exploration of Bobbitt's salt as a sustainable & chemoselective oxidant
Bobbitt's salt is an oxoammonium salt that is easily prepared on large scale from commodity materials. Others have shown that it is capable of a range of oxidative transformations, including those that require the subtle discrimination of oxidizable functional groups. We are interested in further exploring the utility of this green oxidant, both in the research and instructional lab setting. For example, we have studied the oxidation of hydrazides and have worked with colleagues to develop a didactic lab using the reagent.
Medicinal chemistry of phenolic natural products containing fluorinated isosteres
Ginger and turmeric have been reputed to be natural remedies for a variety of ailments for centuries. Although the phenolic constituents responsible for their bioactivity are known (gingerols, shogaols, curcumin), the specific biochemical basis of their activities still not fully understood. We are engaged in an intradepartmental collaboration with the Wilkinson group wherein analogs of these molecules are synthesized with fluorinated isosteres at key positions. These analogs are subjected to various biochemical assays to determine a structure-activity relationships of the analogs of with the overarching aim of better understanding these molecule's mechanism of action.
Funding Support
National Science Foundation Launching Early-Career Academic Pathways in the Mathematical and (NSF LEAPS-MPS): “Exploring the utility of bifunctional silicate-based reagents for visible light-mediated synthesis of heterocycles and biologically relevant molecules” (2023-2025)
Organic Syntheses PUI Faculty Research grant: “Development of homologous dipolar cycloadditions with nitrones and azomethine imines via photoredox-enabled radical polar crossover” (2021-2022)
Thomas Jefferson University Research, Scholarship, and Practice Based Project Seed Grant: “Toward a Better Understanding of the Molecular Basis of Ginger’s Health Benefits: Synthesis and Biological Assay of Metabolically Stabilized Gingerol Derivatives” (2022-2023)
Thomas Jefferson University Nexus Learning Grant: “Implementing a Peer-Led Team Learning (PLTL) Program to Promote a Deeper Sense of Belonging and Epistemic Confidence among Organic Chemistry Students” (2020-2022)