Affiliation:
1. Department of Chemistry, College of Science and Mathematics, Mindanao State University – Iligan Institute of Technology
2. Department of Chemistry, National Sun Yat-sen University
3. Green Hydrogen Research Center, National Sun Yat-sen University
4. Department of Applied and Medicinal Chemistry, Kaohsiung Medical University
Abstract
AbstractThe recent prominence of ketones as handles for sp3-rich radicals has expanded the paradigm of synthetic utility of ketones, putting the ubiquitous functional group once again into the spotlight in recent years. One emerging strategy arose through ketone-derived pro-aromatic reagents in the form of dihydrobenzothiazoline (BTZ), dihydroquinazolinone (DHQZ), dihydropyrazole (DHP), and dihydro-1,2,4-triazole (DHT) as key intermediates for aromaticity-promoted C–C bond homolytic fission. The formed sp3-radicals could then participate in various radical functionalizations, including alkylations, arylations, olefination, alkynylation, silylations, amination, thiolation, and deuteration, among others, either in photocatalytic, thermal, or oxidative conditions. In this review, we highlight the implications and recent advances in using these pro-aromatic reagents in radical group transfer reactions and deconstructive functionalization.1 Introduction2 Aromatization-Driven C–C Bond Scission of Ketones3 Photochemical Reactions of Ketone-Derived Pro-aromatic Reagents4 Non-photochemical Reactions of Ketone-Derived Pro-aromatic Reagents5 Conclusion and Future Outlook
Funder
Ministry of Science and Technology, Taiwan
Ministry of Education of Taiwan