Photoinduced Radical-Polar Crossover of Bicyclo[1.1.0]butanes for the Synthesis of Fluorinated Spirocycles

Fluorinated spirocycles are privileged scaffolds in drug discovery, yet their efficient synthesis remains challenging. Herein, we report a visible-light-driven radical-polar crossover cascade between bicyclo[1.1.0]butanes (BCBs) and bromodifluoroacetamides to access fluorinated spirocyclic succinimides. The reaction proceeds under mild conditions through strain-release ring-opening of the BCB framework followed by intramolecular annulation. This protocol enables rapid access to fluorinated spirocyclic heterocycles with broad substrate scope and good functional group tolerance. Preliminary mechanistic studies support the proposed reaction pathway.

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Journal
Synthesis
Published
2026-05-29
DOI
https://doi.org/10.1055/a-2883-8150
Primary Topic
Radical Photochemical Reactions
Type
article
Field-Weighted Citation Impact
0.00

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article

Photoinduced Radical-Polar Crossover of Bicyclo[1.1.0]butanes for the Synthesis of Fluorinated Spirocycles

Lingling Chu, Ye Yuan, Hui Li, Yuyang Bai et al.
Synthesis
Radical Photochemical Reactions
article

Photoinduced Radical-Polar Crossover of Bicyclo[1.1.0]butanes for the Synthesis of Fluorinated Spirocycles

Lingling Chu, Ye Yuan, Hui Li, Yuyang Bai, Guangying Huang, Shengqing Zhu
article en

Abstract

Fluorinated spirocycles are privileged scaffolds in drug discovery, yet their efficient synthesis remains challenging. Herein, we report a visible-light-driven radical-polar crossover cascade between bicyclo[1.1.0]butanes (BCBs) and bromodifluoroacetamides to access fluorinated spirocyclic succinimides. The reaction proceeds under mild conditions through strain-release ring-opening of the BCB framework followed by intramolecular annulation. This protocol enables rapid access to fluorinated spirocyclic heterocycles with broad substrate scope and good functional group tolerance. Preliminary mechanistic studies support the proposed reaction pathway.

Synthesis
Donghua University (CN)
National Natural Science Foundation of China
Good health and well-being
Openalex Percentile: Top 10%
Radical Photochemical Reactions
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Photoinduced Radical-Polar Crossover of Bicyclo[1.1.0]butanes for the Synthesis of Fluorinated Spirocycles — Lingling Chu, Ye Yuan, et al. · Synthesis (2026) | TGRS Research Map | TGRS