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DOI: 10.1055/a-2197-1909
Ketone-Derived Pro-aromatic Reagents for Radical Group Transfer Reactions and Deconstructive Functionalizations
This work was supported by the Young Scholar Fellowship Program of the Ministry of Science and Technology (MOST 111-2636-M-110-011) and the Yushan Young Scholar Program of the Ministry of Education of Taiwan (H.H.L.).
Dedicated to Prof. Dr. Evelyn Creencia on the occasion of her retirement from the Dept. of Chemistry, Mindanao State University – Iligan Institute of Technology.
Abstract
The 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 Introduction
2 Aromatization-Driven C–C Bond Scission of Ketones
3 Photochemical Reactions of Ketone-Derived Pro-aromatic Reagents
4 Non-photochemical Reactions of Ketone-Derived Pro-aromatic Reagents
5 Conclusion and Future Outlook
Key words
aromatization - radicals - ketones - metallaphotoredox - photoredox - thermal - C–C bond activationPublication History
Received: 22 September 2023
Accepted after revision: 23 October 2023
Accepted Manuscript online:
24 October 2023
Article published online:
27 November 2023
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For representative reviews on C–C bond formations via transition-metal catalysis, see:
For C–C bond formations via organocatalysis, see:
For C–C bond formations via biocatalysis, see: