Citation: Yuping Xiong, Feihua Du, Linghui Zeng, Zhiyuan Chen. I₂/PhI(OAc)₂-assisted oxidative CH amination protocols toward metal-free pragmatic synthesis of pyrrolo[2, 3-b]indoles[J]. Chinese Chemical Letters, ;2023, 34(1): 107569. doi: 10.1016/j.cclet.2022.05.083 shu

I₂/PhI(OAc)₂-assisted oxidative CH amination protocols toward metal-free pragmatic synthesis of pyrrolo[2, 3-b]indoles

Yuping Xiong ^a ,
Feihua Du ^b ,
Linghui Zeng ^{b, *,} ,
Zhiyuan Chen ^{a, b, *,}

a.
College of Chemistry & Chemical Engineering, Jiangxi Normal University, Nanchang 330022, China
b.
School of Medicine, Zhejiang University City College, Hangzhou 310015, China

zenglh@zucc.edu.cn

zchen@jxnu.edu.cn

Received Date: 13 December 2021
Revised Date: 23 May 2022
Accepted Date: 26 May 2022
Available Online: 29 May 2022

Figures(6)

We report herein an I₂/PhI(OAc)₂ catalytic system for the pragmatic construction of CN bonds through CH/NH oxidative coupling protocol. Divergent pyrrolo[2, 3-b]indoles were efficiently prepared via I₂-catalyzed intramolecular C–H amination reactions from (E/Z)-2-indolylenamines under metal-free conditions. Various functional groups are tolerated under mild reaction conditions and the resulting pyrrolo[2, 3-b]indoles were obtained with mostly good to excellent yields. It was interesting to observe that both the (E)- and (Z)-isomers of the starting materials were efficiently transformed into the targeted product. The I⁺-mediated catalytic cycle was proposed based on mechanistic studies for this reaction.
- CH activation,
- CH amination,
- Indole,
- Oxidative cyclization,
- aza-Heterocycle
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通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142

I2/PhI(OAc)2-assisted oxidative CH amination protocols toward metal-free pragmatic synthesis of pyrrolo[2, 3-b]indoles

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通讯作者: 陈斌, bchen63@163.com

I₂/PhI(OAc)₂-assisted oxidative CH amination protocols toward metal-free pragmatic synthesis of pyrrolo[2, 3-b]indoles