Accessing SuFExable Cyclobutane‐Fused Indolines via Photocatalytic Intermolecular [2+2] Cycloaddition of Indoles

Indoline‐fused polycycles are commonly found as a key structural component in numerous natural products and biologically active compounds. In recent times, the incorporation of sulfonyl fluoride groups has drawn significant attention in research due to their potential to enhance or confer new biolog...

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Bibliographic Details
Published in:Advanced synthesis & catalysis 2024-07, Vol.366 (14), p.3117-3122
Main Authors: Wei, Rongbiao, Pei, Guanhua, Huang, Yao, Liao, Saihu
Format: Article
Language:English
Subjects:
Chemical synthesis
Conjugation
Cycloaddition
Cyclobutane
Functional groups
Heterocyclic compounds
Indoles
Indolines
Intermolecular [2+2] cycloaddition
Natural products
Photocatalysis
SuFEx click reactions
Sulfonyl fluorides
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Summary:Indoline‐fused polycycles are commonly found as a key structural component in numerous natural products and biologically active compounds. In recent times, the incorporation of sulfonyl fluoride groups has drawn significant attention in research due to their potential to enhance or confer new biological activities to molecules. In this study, we report the development of a modular approach for synthesizing FSO2‐functionalized cyclobutane‐fused indolines by employing an intermolecular [2+2] cycloaddition reaction between indoles and SuFExable ethenesulfonyl fluoride under triplet energy‐transfer catalysis. This method features mild reaction conditions, metal‐free photocatalysts, and excellent tolerance to various functional groups. Moreover, we demonstrate the feasibility of further modifying the FSO2‐functionalized indoline products via SuFEx click reactions, enabling their conjugation with other molecules.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.202400274