Synthesis of FSO2-Functionalized Oxindoles via a Radical Fluorosulfonylation/Intramolecular Arylation Cascade

Na Yang; Guanhua Pei; Hao Li; Junwei Han; Peng Wang; Lili Xie; Saihu Liao

doi:10.1055/a-2409-5678

Synthesis, Table of Contents

Synthesis 2025; 57(05): 999-1006
DOI: 10.1055/a-2409-5678

paper

SuFEx Chemistry

Synthesis of FSO₂-Functionalized Oxindoles via a Radical Fluorosulfonylation/Intramolecular Arylation Cascade

Na Yang

^aKey Laboratory of Molecule Synthesis and Function Discovery, College of Chemistry, Fuzhou University, 2 Xueyuan Road, Fuzhou 350116, P. R. of China

,

Guanhua Pei

^aKey Laboratory of Molecule Synthesis and Function Discovery, College of Chemistry, Fuzhou University, 2 Xueyuan Road, Fuzhou 350116, P. R. of China

,

Hao Li

^aKey Laboratory of Molecule Synthesis and Function Discovery, College of Chemistry, Fuzhou University, 2 Xueyuan Road, Fuzhou 350116, P. R. of China

,

Junwei Han

^aKey Laboratory of Molecule Synthesis and Function Discovery, College of Chemistry, Fuzhou University, 2 Xueyuan Road, Fuzhou 350116, P. R. of China

,

Peng Wang

^aKey Laboratory of Molecule Synthesis and Function Discovery, College of Chemistry, Fuzhou University, 2 Xueyuan Road, Fuzhou 350116, P. R. of China

^bKey Laboratory of Green and Precise Synthetic Chemistry and Applications, Ministry of Education, Huaibei Normal University, Huaibei, Anhui 235000, P. R. of China

,

Lili Xie

^aKey Laboratory of Molecule Synthesis and Function Discovery, College of Chemistry, Fuzhou University, 2 Xueyuan Road, Fuzhou 350116, P. R. of China

,

Saihu Liao ∗

^aKey Laboratory of Molecule Synthesis and Function Discovery, College of Chemistry, Fuzhou University, 2 Xueyuan Road, Fuzhou 350116, P. R. of China

^cState Key Laboratory of Physical Chemistry of Solid Surfaces, Xiamen University, Xiamen 361005, P. R. of China

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Abstract

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Abstract

Herein, we report the development of a FSO₂ radical initiated tandem cyclization reaction under visible light photoredox catalysis, which allows for a facile access to FSO₂-functionalized oxindoles from N-arylacrylamides. This reaction features mild reaction conditions, readily available starting materials, and SuFExable products. The introduction of sulfonyl fluoride groups into oxindoles could be of interest for related study in the context of discovering new bioactive molecules.

Key words

FSO₂ radicals - photoredox catalysis - oxindoles - SuFEx - click chemistry

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References

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