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.

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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

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article

Ketone-Derived Dihydroquinazolinones as Carbamoyl Radical Precursors for Photoredox Amidation of Electron-Deficient Alkenes

Min Hong, Xiaoming Zhou, Qian Li, Lei Li et al.
The Journal of Organic Chemistry
Radical Photochemical Reactions
article

Ketone-Derived Dihydroquinazolinones as Carbamoyl Radical Precursors for Photoredox Amidation of Electron-Deficient Alkenes

Min Hong, Xiaoming Zhou, Qian Li, Lei Li, Yongchao Lu, Zhe Jia, Xiu-Long Wu, Zi-Min Hao
article en

Abstract

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.

The Journal of Organic ChemistryVol. 91(18)
Liaocheng University (CN), Shandong Academy of Pharmaceutical Sciences (CN)
National Natural Science Foundation of China
Clean water and sanitation
Openalex Percentile: Top 19%
Radical Photochemical Reactions
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