Research Projects

Skeletal editing has emerged as a transformative strategy in synthetic chemistry, enabling the precise modification of molecular frameworks through the insertion, deletion, or substitution of atoms within cyclic systems. This approach allows direct access to structurally and functionally diverse compounds from common precursors, providing a powerful platform for late-stage diversification, scaffold hopping, and molecular innovation in drug discovery and materials science. Recent advances have demonstrated the potential of skeletal editing in heterocycle synthesis. Notably, the photocatalytic transformation of furans into pyrroles via nitrogen atom insertion has shown that C–O to C–N atom swapping can efficiently remodel aromatic systems while preserving overall molecular topology. Similarly, C–N skeletal editing strategies have been successfully applied to indoles and benzofurans, converting them into indazoles, benzisoxazoles, and benzoxazoles through selective nitrogen incorporation. Building on these precedents, this project proposes two new skeletal editing methodologies: (1) a photocatalytic furan-to-thiophene transformation through O-to-S atom swapping using electrophilic sulfur donors such as Lawesson’s reagent or elemental sulfur, and (2) a benzothiophene-to-benzothiazole/benzoisothiazole strategy involving photoirradiation- or oxidation-induced C2–C3 bond cleavage, followed by trapping of reactive intermediates with nitrogen nucleophiles such as hydroxylamine, azides, or thioamides. Both methodologies will be supported by extensive reaction optimization, substrate scope exploration, and mechanistic elucidation using DFT calculations. Products will be characterized using NMR, HRMS, IR, and X-ray crystallography where applicable. Collectively, these studies aim to develop flexible and effective synthetic protocols for heterocycle remodeling, contributing significantly to the synthesis of novel bioactive compounds.