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Metal-free, Phosphoric Acid-catalyzed Regioselective 1,6-Hydroarylation of para-Quinone Methides with Indoles in Water
被引:11
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
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.
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页数:13
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