Metal-free dearomative [5+2]/[2+2] cycloaddition of 1H-indoles with ortho-(trimethylsilyl)aryl triflates

被引：10

作者：

Chen, Xinyu ^{[1
]}

Yang, Na ^{[1
]}

Zeng, Wen ^{[1
]}

Wang, Lei ^{[1
,2
,3
,4
]}

Li, Pinhua ^{[1
]}

Li, Hongji ^{[1
,4
]}

机构：

[1] Huaibei Normal Univ, Dept Chem, Huaibei 235000, Anhui, Peoples R China

[2] Taizhou Univ, Adv Res Inst, Taizhou 318000, Zhejiang, Peoples R China

[3] Taizhou Univ, Dept Chem, Taizhou 318000, Zhejiang, Peoples R China

[4] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China

来源：

CHEMICAL COMMUNICATIONS | 2021年 / 57卷 / 57期

基金：

美国国家科学基金会;

关键词：

C-H; ANNULATION; ARYNES; ARYLATION; INDOLES; AGENTS;

D O I：

10.1039/d1cc02550c

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Herein, we report a mild dearomative [5+2]/[2+2] cycloaddition of 1H-indoles with ortho-(trimethylsilyl)aryl triflates. The unique [5+2] cycloaddition enables the synthesis of a series of dibenzo[b,e]azepine derivatives in moderate to good yields. Increasing the steric hindrance at the C2-position of 1H-indoles leads to the [2+2] cycloaddition. Mechanistic investigations support that the reaction of 1H-indoles with arynes undergoes a [2+2] cycloaddition step, followed by a ring expansion to the [5+2] cycloaddition product.

引用

页码：7047 / 7050

页数：4

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