Electrophotocatalytic Radical Cascade Reaction for the Synthesis of Trifluoromethylated Spirocyclobutyl Oxindoles

We report an electrophotocatalytic strategy for the radical fluoroalkylation and spirocyclization of bicyclo[1.1.0]butanes. This synergistic method leverages the energy of electricity and light to generate fluoroalkyl radicals from inexpensive Langlois' reagents under mild, metal-free conditions. Overcoming the limitations of conventional electrochemistry and photoredox catalysis, this protocol provides efficient access to a diverse array of valuable spirocyclobutyl oxindoles bearing CF<sub>3</sub>, CF<sub>2</sub>H, and long-chain perfluoroalkyl groups with high functional group tolerance. Mechanistic studies confirm the radical cascade pathway and the essential role of the electrophotocatalytic system.

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Publication Details

Journal
Organic Letters
Published
2025-10-13
DOI
https://doi.org/10.1021/acs.orglett.5c03594
Citations
3
Primary Topic
Fluorine in Organic Chemistry
Type
article
Field-Weighted Citation Impact
2.37
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article

Electrophotocatalytic Radical Cascade Reaction for the Synthesis of Trifluoromethylated Spirocyclobutyl Oxindoles

Biplab Maji, Rajib Maity
3 citations
Organic Letters
Fluorine in Organic Chemistry
2.37
article

Electrophotocatalytic Radical Cascade Reaction for the Synthesis of Trifluoromethylated Spirocyclobutyl Oxindoles

Biplab Maji, Rajib Maity
article en
3 citations

Abstract

We report an electrophotocatalytic strategy for the radical fluoroalkylation and spirocyclization of bicyclo[1.1.0]butanes. This synergistic method leverages the energy of electricity and light to generate fluoroalkyl radicals from inexpensive Langlois' reagents under mild, metal-free conditions. Overcoming the limitations of conventional electrochemistry and photoredox catalysis, this protocol provides efficient access to a diverse array of valuable spirocyclobutyl oxindoles bearing CF<sub>3</sub>, CF<sub>2</sub>H, and long-chain perfluoroalkyl groups with high functional group tolerance. Mechanistic studies confirm the radical cascade pathway and the essential role of the electrophotocatalytic system.

Organic LettersVol. 27(42)
Indian Institute of Science Education and Research Kolkata (IN)
Openalex Percentile: Top 10%
Fluorine in Organic Chemistry
2.37
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Electrophotocatalytic Radical Cascade Reaction for the Synthesis of Trifluoromethylated Spirocyclobutyl Oxindoles — Biplab Maji, Rajib Maity · Organic Letters (2025) | TGRS Research Map | TGRS