Metal-free, Phosphoric Acid-catalyzed Regioselective 1,6-Hydroarylation of para-Quinone Methides with Indoles in Water

被引：13

作者：

Xiong, Biquan ^{[1
,2
]}

Si, Lulu ^{[1
]}

Liu, Yu ^{[1
]}

Xu, Weifeng ^{[1
]}

Jiang, Tao ^{[1
]}

Cao, Fan ^{[1
]}

Ke-Wen Tang ^{[1
]}

Wai-Yeung Wong ^{[2
]}

机构：

[1] Hunan Inst Sci & Technol, Dept Chem & Chem Engn, Yueyang 414006, Peoples R China

[2] Hong Kong Polytech Univ, Dept Appl Biol & Chem Technol, Hung Hom, Hong Kong, Peoples R China

来源：

CHEMISTRY-AN ASIAN JOURNAL | 2022年 / 17卷 / 09期

基金：

中国国家自然科学基金;

关键词：

1; 6-hydroarylation; bronsted-acid catalysis; green media; indoles; para-quinone methides; 1,6-CONJUGATE ADDITION; 2+1 ANNULATION; DERIVATIVES; BIS(INDOLYL)METHANE; ARYLATION;

D O I：

10.1002/asia.202200042

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An efficient, cheap and green protocol for the highly regioselective 1,6-hydroarylation of para-quinone methides (p-QMs) with indoles at the C-3 position has been established by phosphoric acid catalysis in water under transition-metal-free reaction conditions. A wide range of indole derivatives and para-quinone methides (p-QMs) are compatible for the reaction, affording the corresponding 1,6-hydroarylation products with good to excellent yields. The possible mechanism of the reaction has been explored through step-by-step control experiments. The protocol is convenient for practical applications, leading to a safe, green and feasible way for the formation of C-3 diarylmethyl functionalized indole derivatives.

引用

页数：13

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