Near-Infrared-Light-Induced Iron(I) Dimer-Enabled Radical Cascade Reactions of Fluoroalkyl Bromides for the Synthesis of Ring-Fused Quinazolinones

The use of an earth-abundant and inexpensive iron complex as a catalyst, coupled with near-infrared (NIR) light as the energy source, for radical reactions with alkyl halides has been far less developed. In this study, we report NIR light-mediated iron(I) dimer-catalyzed radical cascade reactions of fluoroalkyl bromides for the synthesis of ring-fused quinazolinones bearing a difluoromethyl group. In this process, the 3-bromo-1,10-phenanthroline ligand facilitates the reactivity of [CpFe(CO)<sub>2</sub>]<sub>2</sub>, thereby improving the efficiency of the reaction.

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Publication Details

Journal
Organic Letters
Published
2024-09-06
DOI
https://doi.org/10.1021/acs.orglett.4c03087
Citations
13
Primary Topic
Radical Photochemical Reactions
Type
article
Field-Weighted Citation Impact
3.25

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article

Near-Infrared-Light-Induced Iron(I) Dimer-Enabled Radical Cascade Reactions of Fluoroalkyl Bromides for the Synthesis of Ring-Fused Quinazolinones

Xiang‐Yu Chen, Qiang Liu, Zhixiang Wang, Xiao-Di Su et al.
13 citations
Organic Letters
Radical Photochemical Reactions
3.25
article

Near-Infrared-Light-Induced Iron(I) Dimer-Enabled Radical Cascade Reactions of Fluoroalkyl Bromides for the Synthesis of Ring-Fused Quinazolinones

Xiang‐Yu Chen, Qiang Liu, Zhixiang Wang, Xiao-Di Su, Jin‐Tang Cheng
article en
13 citations

Abstract

The use of an earth-abundant and inexpensive iron complex as a catalyst, coupled with near-infrared (NIR) light as the energy source, for radical reactions with alkyl halides has been far less developed. In this study, we report NIR light-mediated iron(I) dimer-catalyzed radical cascade reactions of fluoroalkyl bromides for the synthesis of ring-fused quinazolinones bearing a difluoromethyl group. In this process, the 3-bromo-1,10-phenanthroline ligand facilitates the reactivity of [CpFe(CO)<sub>2</sub>]<sub>2</sub>, thereby improving the efficiency of the reaction.

Organic LettersVol. 26(37)
Chinese Academy of Medical Sciences & Peking Union Medical College (CN), Binzhou People's Hospital (CN), University of Chinese Academy of Sciences (CN)
National Natural Science Foundation of China, China Academy of Chinese Medical Sciences, University of Chinese Academy of Sciences, Fundamental Research Funds for the Central Universities, Beijing National Laboratory for Molecular Sciences
Clean water and sanitation
Openalex Percentile: Top 7%
Radical Photochemical Reactions
3.25
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