Synthesis, Characterization, and DFT Studies of NHC-Derived Amide-Functionalized Organoselenium Compounds

The NHC-Se scaffold has emerged as an intriguing target, opening new avenues for discovering compounds that could significantly improve public health. Recently, extensive efforts have been made to synthesize NHC-Se-based organic compounds for various biomedical applications. Herein, we disclose a straightforward method to access a series of new N-heterocyclic carbene (NHC)-derived organoselenium molecules functionalized with an amide moiety. The parent NHC-Se adduct with a pendent ester moiety is sufficiently activated to facilitate a base- and additive-free ester-to-amide bond transformation. Furthermore, the use of PEG 3550, a biocompatible solvent, enhances reaction efficiency and simplifies the workup. This approach employs a broad spectrum of aliphatic amines with good functional group tolerance, offering a versatile and ecofriendly method for extending chemical space around organoselenium compounds. Additionally, density functional theory (DFT) calculations provide insights into the electronic properties, stability, and reactivity profiles of the synthesized compounds, suggesting their promising potential for applications in biomedical fields.