Trichloroisocyanuric Acid Induced Chlorine Radical Cascade Chlorination­/Carbocyclization of Acrylamides: Constructing Chlorinated Oxindoles by C–Cl and C–C Bond-Forming Reactions

Yingpeng Su; Lindan Cao; Ya Shi; Yawei Feng; Wenxuan Xue; Guiyan Cao; Ke-Hu Wang; Danfeng Huang; Congde Huo; Yulai Hu

doi:10.1055/s-0037-1610868

Synthesis, Table of Contents

Synthesis 2019; 51(11): 2331-2338
DOI: 10.1055/s-0037-1610868

paper

Trichloroisocyanuric Acid Induced Chlorine Radical Cascade Chlorination/Carbocyclization of Acrylamides: Constructing Chlorinated Oxindoles by C–Cl and C–C Bond-Forming Reactions

Yingpeng Su *

^aCollege of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou, Gansu, 730070, P. R. of China Email: Suyp51@nwnu.edu.cn

,

Lindan Cao

^aCollege of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou, Gansu, 730070, P. R. of China Email: Suyp51@nwnu.edu.cn

,

Ya Shi

^aCollege of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou, Gansu, 730070, P. R. of China Email: Suyp51@nwnu.edu.cn

,

Yawei Feng

^aCollege of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou, Gansu, 730070, P. R. of China Email: Suyp51@nwnu.edu.cn

,

Wenxuan Xue

^aCollege of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou, Gansu, 730070, P. R. of China Email: Suyp51@nwnu.edu.cn

,

Guiyan Cao

^aCollege of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou, Gansu, 730070, P. R. of China Email: Suyp51@nwnu.edu.cn

,

Ke-Hu Wang

^aCollege of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou, Gansu, 730070, P. R. of China Email: Suyp51@nwnu.edu.cn

,

Danfeng Huang

^aCollege of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou, Gansu, 730070, P. R. of China Email: Suyp51@nwnu.edu.cn

,

Congde Huo

^aCollege of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou, Gansu, 730070, P. R. of China Email: Suyp51@nwnu.edu.cn

,

Yulai Hu

^aCollege of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou, Gansu, 730070, P. R. of China Email: Suyp51@nwnu.edu.cn

^bState Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, P. R. of China

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Abstract

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Abstract

A metal- and additive-free strategy for the synthesis of oxindoles has been achieved through a chlorine radical-induced cascade chlorination/carbocyclization of N-aryl acrylamides. Trichloroisocyanuric acid (TCCA) is used as both radical initiator and chlorine source. A wide range of substrates can be applied in this process to directly afford chlorinated oxindoles via C–Cl and C–C bond formation.

Key words

trichloroisocyanuric acid - N-aryl acrylamide - chlorination - cascade carbocyclization reaction - oxindoles

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References

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Supplementary Material

Supporting Information

Trichloroisocyanuric Acid Induced Chlorine Radical Cascade Chlorination­/Carbocyclization of Acrylamides: Constructing Chlorinated Oxindoles by C–Cl and C–C Bond-Forming Reactions

Trichloroisocyanuric Acid Induced Chlorine Radical Cascade Chlorination/Carbocyclization of Acrylamides: Constructing Chlorinated Oxindoles by C–Cl and C–C Bond-Forming Reactions