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

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

共 29 条

[21] Recyclable Bismuth Complex Catalyzed 1,6-Conjugate Addition of Various Nucleophiles to para-Quinone Methides: Expedient Access to Unsymmetrical Diaryl- and Triarylmethanes [J].

Liang, Xianghao ;

Xu, Haiyan ;

Li, Hanlin ;

Chen, Lizhuang ;

Lu, Hongfei .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2020, 2020 (02) :217-226

[22] 1,6-Aza-Michael addition of para-quinone methides with N-heterocycles catalyzed by Zn(OTf)2: A regioselective approach to N-diarylmethyl-substituted heterocycles [J].

Guin, Soumitra ;

Saha, Hemonta K. ;

Patel, Ashvani K. ;

Gudimella, Santosh K. ;

Biswas, Subhankar ;

Samanta, Sampak .

TETRAHEDRON, 2020, 76 (28-29)

[23] Direct access to a,a′-diarylated ketones through N-heterocyclic carbene-catalyzed 1,6-addition of aromatic aldehydes to para-quinone methides [J].

Zhang, Guifu ;

Jiang, Longxiang ;

Shi, Wenjuan ;

Zhou, Meiling ;

Qiu, Fenghao ;

Sun, Shaofa ;

Wang, Jian ;

Guo, Haibing .

SYNTHETIC COMMUNICATIONS, 2017, 47 (08) :803-810

[24] 1,6-Conjugate hydrogenation of para-quinone methides to phenol-containing diaryl- and triarylmethanes under atmospheric pressure catalyzed by a metal-ligand bifunctional iridium catalyst [J].

Zhao, Guoqiang ;

Xu, Xiangchao ;

Zhang, Jin ;

Dong, Beixuan ;

Wang, Wenli ;

Zhou, Wenbo ;

Shi, Qixun ;

Li, Feng .

JOURNAL OF CATALYSIS, 2024, 440

[25] Phosphine-Catalyzed γ′-Carbon 1,6-Conjugate Addition of α-Succinimide Substituted Allenoates with Para-Quinone Methides: Synthesis of 4-Diarylmethylated 3,4-Disubstituted Maleimides [J].

Gao, Zhenzhen ;

Zhou, Xiaoming ;

Liu, Dandan ;

Nie, Baoshen ;

Lu, Hanchong ;

Chen, Xiaotong ;

Wu, Jiahui ;

Li, Lei ;

Wang, Xuekun .

MOLECULES, 2024, 29 (11)

[26] Metal-Free Approach for Oxa-spirocyclohexadienones through [3+2]/[4+2] ipso-Cyclization of para-Quinone Methides with Halo Alcohols [J].

Gaikwad, Ramesh A. ;

Savekar, Amol T. ;

Waghmode, Suresh B. .

JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (14) :9987-10001

[27] Metal-Free, Bronsted Acid-Catalyzed Formal [3+2] Annulation of Quinone Monoacetals with 2-Naphthols [J].

Jacob, Anu ;

Roy, Tony ;

Kaicharla, Trinadh ;

Biju, Akkattu T. .

JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (20) :11269-11274

[28] Sc(OTf)3-Catalyzed 1,6-Conjugate Addition of Thiols to δ-CF3-δ-aryl-disubstituted para-Quinone Methides: Efficient Construction of Diarylmethane Thioethers [J].

Li, Hua ;

Pang, Jingxiang ;

Liu, Huazheng ;

Zhao, Changyin ;

Li, Song ;

Wang, Hengshan ;

Liu, Xigong .

CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2021, 41 (08) :3134-3143

[29] Efficient construction of polycyclic chromans through 4-methylbenzenesulfonic acid mediated domino 1,6-addition/oxa-Mannich reaction of ortho-hydroxyphenyl substituted para-quinone methides and cyclic enamides [J].

Wang, Zhen-Hua ;

Zhang, Xia-Yan ;

You, Yong ;

Zhao, Jian-Qiang ;

Zhou, Ming-Qiang ;

Zhang, Xiao-Mei ;

Xu, Xiao-Ying ;

Yuan, Wei-Cheng .

TETRAHEDRON, 2019, 75 (25) :3456-3462

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