Photocatalytic Radical Relay Strategy for the Synthesis of Allylic <i>gem</i> -Difluorides via 1,4-Difunctionalization of <i>gem</i> -Difluorobuta-1,3-dienes

Fluorine-containing organic compounds are vital in bioactive molecules and materials, with allylic <i>gem</i>-difluorides as key motifs in drugs. Herein, we report an efficient photocatalytic strategy for the synthesis of allylic <i>gem</i>-difluorides using bench-stable oxime esters as dual alkyl or aryl/iminyl radical precursors. The system exhibits a broad substrate scope with 39-87% yields and gram-scale scalability. Meanwhile, this methodology exhibits high regioselectivity and <i>E</i> selectivity. Additionally, the products can be further transformed into other functionalized products.

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Publication Details

Journal
Organic Letters
Published
2026-01-26
DOI
https://doi.org/10.1021/acs.orglett.5c05446
Primary Topic
Fluorine in Organic Chemistry
Type
article
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article

Photocatalytic Radical Relay Strategy for the Synthesis of Allylic gem -Difluorides via 1,4-Difunctionalization of gem -Difluorobuta-1,3-dienes

Luxuan Xu, Shenting Xu, Nanxi Wang, Zhen Zhang et al.
Organic Letters
Fluorine in Organic Chemistry
article

Photocatalytic Radical Relay Strategy for the Synthesis of Allylic gem -Difluorides via 1,4-Difunctionalization of gem -Difluorobuta-1,3-dienes

Luxuan Xu, Shenting Xu, Nanxi Wang, Zhen Zhang, Kui Zhang, Lingchao Cai, Yan Lin, Xu Lu
article en

Abstract

Fluorine-containing organic compounds are vital in bioactive molecules and materials, with allylic <i>gem</i>-difluorides as key motifs in drugs. Herein, we report an efficient photocatalytic strategy for the synthesis of allylic <i>gem</i>-difluorides using bench-stable oxime esters as dual alkyl or aryl/iminyl radical precursors. The system exhibits a broad substrate scope with 39-87% yields and gram-scale scalability. Meanwhile, this methodology exhibits high regioselectivity and <i>E</i> selectivity. Additionally, the products can be further transformed into other functionalized products.

Organic LettersVol. 28(5)
Nanjing University of Chinese Medicine (CN), Nanjing Forestry University (CN), Intelligent Synthetic Biology Center (KR), Institute of Chemical Industry of Forest Products (CN)
Openalex Percentile: Top 77%
Fluorine in Organic Chemistry
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Photocatalytic Radical Relay Strategy for the Synthesis of Allylic <i>gem</i> -Difluorides via 1,4-Difunctionalization of <i>gem</i> -Difluorobuta-1,3-dienes — Luxuan Xu, Shenting Xu, et al. · Organic Letters (2026) | TGRS Research Map | TGRS