Citation: Rui-Ying Zhang, Meng-Meng Xu, Hai-Yan Li, Xiao-Ping Xu, Shun-Jun Ji. Cascade reaction involving intramolecular oxygen-migration: Efficient synthesis of 3-allylidene-indolin-2-one compounds under metal-free conditions[J]. Chinese Chemical Letters, ;2021, 32(1): 433-436. doi: 10.1016/j.cclet.2020.03.070 shu

Cascade reaction involving intramolecular oxygen-migration: Efficient synthesis of 3-allylidene-indolin-2-one compounds under metal-free conditions

Rui-Ying Zhang ^a ,
Meng-Meng Xu ^a ,
Hai-Yan Li ^b ,
Xiao-Ping Xu ^{a, *} ,
Shun-Jun Ji ^{a, *}

a.
Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science & Collaborative Innovation Center of Suzhou Nano Science and Technology, Soochow University, Suzhou 215123, China
b.
Analysis and Testing Center, Soochow University, Suzhou 215123, China

xuxp@suda.edu.cn

shunjun@suda.edu.cn

Received Date: 8 February 2020
Revised Date: 18 March 2020
Accepted Date: 27 March 2020
Available Online: 11 April 2020

Figures(8)

An efficient synthesis of 3-(diarylallylidene)oxindoles from 3-(1H-indol-3-yl)-1, 1-diarylpropan-1-ol under metal-free conditions is described. NBS serves as a critical medium leading to a facile oxygen-migration in the transformation. The protocol has advantages of high efficiency, simple opreation, mild reaction conditions, good atom-economy, wide substrate scope and good yields of products. A detailed mechanism is proposed after careful investigation.
- NBS mediated,
- Oxygen migration,
- Conjugate double bonds,
- Multi-step cascade
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