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
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页数：13
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