Ketone-Derived Dihydroquinazolinones as Carbamoyl Radical Precursors for Photoredox Amidation of Electron-Deficient Alkenes
A visible-light photoredox strategy for the amidation of electron-deficient alkenes is disclosed, enabled by ketone-derived, carbamoyl-functionalized dihydroquinazolinones as a new class of carbamoyl radical precursors. Under mild conditions, these readily accessible proaromatic reagents undergo aromatization-promoted C-C bond cleavage to generate carbamoyl radicals, which engage in efficient conjugate addition to activated olefins, delivering diverse amide products. The protocol features a broad substrate scope, accommodating tertiary, secondary, and primary carbamoyl radicals and a wide range of electron-deficient alkenes, including sterically demanding and highly functionalized substrates. This work expands the reactivity profile of dihydroquinazolinones and provides a general, operationally simple platform for amide synthesis via C-C bond formation under visible-light photoredox catalysis.
Authors
- Min Hong (ORCID: https://orcid.org/0009-0000-4018-5415)
- Xiaoming Zhou
- Qian Li (ORCID: https://orcid.org/0000-0002-4847-4892)
- Lei Li (ORCID: https://orcid.org/0000-0002-9729-2278)
- Yongchao Lu (ORCID: https://orcid.org/0000-0002-6924-181X)
- Zhe Jia
- Xiu-Long Wu
- Zi-Min Hao
Institutions
- Liaocheng University (CN)
- Shandong Academy of Pharmaceutical Sciences (CN)
Publication Details
- Journal
- The Journal of Organic Chemistry
- Published
- 2026-04-27
- DOI
- https://doi.org/10.1021/acs.joc.6c00284
- Primary Topic
- Radical Photochemical Reactions
- Type
- article
- Field-Weighted Citation Impact
- 0.00
Funders
- National Natural Science Foundation of China