Radical reagents can be utilized for the conversion of unactivated alkyl C–H bonds into reactive species that can lead to the formation of new C–C bonds. In this project, new radical reagents belonging to a specific group called hydrogen atom transfer (HAT) reagents are designed and synthesized for the purpose of Csp3-H bond functionalization. The initial steps focus on the development of new N–F containing precursors from commercially available aromatic compounds using electrophilic fluorination. N-tert-butyl amidyl or N-tert-butyl sulfonamidyl backbones are especially of interest due to the success of similar HAT regents in literature. The N-F bonds can be cleaved homolytically in the presence of a catalyst, such as Copper, unveiling a reactive amidyl radical and a metal-halogen complex. The N radical can then abstract a hydrogen atom from substrates, thus activating the highly stable C–H bond. The analysis of the synthesized reagents is performed using H-NMR, C-NMR, and FT-IR analysis.

Development of new hydrogen atom transfer reagents for catalytic Csp3–H functionalization

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