Organophotoredox-Catalyzed Fluoroalkylation of Morita–Baylis–Hillman Adducts Using Quaternary Fluoroalkyl Alcohols as the Fluoroalkylating Reagents

Photoredox-enabled fluoroalkylation of MBH adducts using quaternary fluoroalkyl alcohols as the fluoroalkylating radical reagents is described. The facile protocol displays excellent functional group tolerance toward a series of synthetic allyl scaffolds containing fluoroalkyl groups under mild conditions. The alternative wavelength of visible light delivers the desired product with different yields and <i>Z/E</i> selectivities. A radical pathway involving an O-centered radical that induces β-scission to form the key fluoroalkyl radical is proposed in this transformation.

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2025-10-15
DOI
https://doi.org/10.1021/acs.joc.5c01991
Primary Topic
Fluorine in Organic Chemistry
Type
article
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article

Organophotoredox-Catalyzed Fluoroalkylation of Morita–Baylis–Hillman Adducts Using Quaternary Fluoroalkyl Alcohols as the Fluoroalkylating Reagents

Qiang Zhao, Xianchao Du, Wenchao Gao, Cun‐Duo Tang et al.
The Journal of Organic Chemistry
Fluorine in Organic Chemistry
article

Organophotoredox-Catalyzed Fluoroalkylation of Morita–Baylis–Hillman Adducts Using Quaternary Fluoroalkyl Alcohols as the Fluoroalkylating Reagents

Qiang Zhao, Xianchao Du, Wenchao Gao, Cun‐Duo Tang, Ting Li, Wenguang Li, Yong Teng, Xin Li
article en

Abstract

Photoredox-enabled fluoroalkylation of MBH adducts using quaternary fluoroalkyl alcohols as the fluoroalkylating radical reagents is described. The facile protocol displays excellent functional group tolerance toward a series of synthetic allyl scaffolds containing fluoroalkyl groups under mild conditions. The alternative wavelength of visible light delivers the desired product with different yields and <i>Z/E</i> selectivities. A radical pathway involving an O-centered radical that induces β-scission to form the key fluoroalkyl radical is proposed in this transformation.

The Journal of Organic ChemistryVol. 90(42)
Institute of Catalysis and Petrochemistry (RU), Nanyang Normal University (CN)
Openalex Percentile: Top 78%
Fluorine in Organic Chemistry
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Organophotoredox-Catalyzed Fluoroalkylation of Morita–Baylis–Hillman Adducts Using Quaternary Fluoroalkyl Alcohols as the Fluoroalkylating Reagents — Qiang Zhao, Xianchao Du, et al. · The Journal of Organic Chemistry (2025) | TGRS Research Map | TGRS