Research Projects

Skeletal editing has rapidly emerged as a transformative tool in synthetic chemistry, allowing for the precise reconfiguration of molecular frameworks and the construction of complex, bioactive molecules. While substantial progress has been achieved in aromatic and heteroaromatic systems through strategies such as atom insertion and radical-mediated processes, similar transformations involving strained cyclic aliphatic structures remain significantly underdeveloped. This project hypothesizes that the inherent ring strain in alkyne-functionalized bicyclic compounds (BCPs) can be strategically utilized under visible-light photoredox and dual catalysis to initiate radical cascades and insertion pathways. This approach aims to facilitate the construction of valuable vinylidenecyclobutanes (VDCBs), bicyclo[3.1.1]heptanes, and azabicyclo[3.1.1]heptanes. These molecular scaffolds not only enrich the three-dimensional (3D) chemical space but also provide new opportunities in medicinal chemistry as rigid, bioisosteric frameworks. The central aim of this research is to develop a range of skeletal editing methodologies for functionalizing strained BCP cores. This will involve radical bifunctionalization, dual catalytic cross-coupling, and boryl radical-induced annulation, allowing for access to complex, pharmaceutically relevant scaffolds. Overall, these novel methods are expected to provide innovative solutions for late-stage functionalization and scaffold hopping in medicinal chemistry, thereby expanding the 3D chemical space accessible for drug discovery.