Date of Graduation
12-2025
Document Type
Dissertation
Degree Name
Doctor of Philosophy in Chemistry (PhD)
Degree Level
Graduate
Department
Chemistry & Biochemistry
Advisor/Mentor
Zheng, Nan
Committee Member
He, Maggie
Second Committee Member
McIntosh, Matt
Third Committee Member
Kilyanek, Stefan
Keywords
Amines; EBX; Functionalization; Photoredox; Radical
Abstract
Remote functionalization of C-C bonds opens a versatile plethora of innovations for chemical synthesis, drug design, and material science. We have enabled a distal alkynylation of C-C bonds via ring opening of pro-aromatic 2-spiro-dihydroquinazolinones and benzodihydrothiadazines by ethynylbenziodoxolones (EBX) at room temperature under photoredox catalysis. The ring-opening produces a gamma distonic radical cation in which the radical moiety undergoes a β-radical addition onto EBX, resulting in alkynylated quinazolinones and benzothiadiazines. High efficiency and complete regioselectivity are achieved in remote C-C bond functionalization.
Citation
Hernandez Sanchez, F. (2025). Photoredox-mediated C–C Bond Cleavage in Dihydroquinazolinones: Generation and Reactivity of Amine Distonic Radical Cations with EBX as Radical Acceptors. Graduate Theses and Dissertations Retrieved from https://scholarworks.uark.edu/etd/6063
