Decarboxylative/decarbonylative C3-acylation of indoles via photocatalysis: a simple and efficient route to 3-acylindoles

被引：86

作者：

Shi, Qing ^{[1
]}

Li, Pinhua ^{[1
]}

Zhu, Xianjin ^{[1
]}

Wang, Lei ^{[1
,2
]}

机构：

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

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

来源：

GREEN CHEMISTRY | 2016年 / 18卷 / 18期

基金：

中国国家自然科学基金;

关键词：

LIGHT PHOTOREDOX CATALYSIS; ALPHA-OXOCARBOXYLIC ACIDS; FRIEDEL-CRAFTS ACYLATION; N-H INDOLES; VISIBLE-LIGHT; C-H; ROSE-BENGAL; OXIDATIVE CYCLIZATION; SUBSTITUTED INDOLES; COUPLING REACTIONS;

D O I：

10.1039/c6gc00516k

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A simple and efficient strategy for the preparation of 3-acylindoles via visible- light promoted C3-acylation of free (NH)- and N-substituted indoles with alpha- oxocarboxylic acids was developed. The reaction tolerates a wide range of functional groups, and the corresponding 3-acylindoles were obtained in high yields under mild conditions.

引用

页码：4916 / 4923

页数：8

共 11 条

[1] Acylation of indoles via photoredox catalysis: a route to 3-acylindoles
Gu, Lijun
Jin, Cheng
Liu, Jiyan
Zhang, Hongtao
Yuan, Minglong
Li, Ganpeng
GREEN CHEMISTRY, 2016, 18 (05) : 1201 - 1205
[2] Cerium(III)-catalyzed C3-acylation of indoles with nitroolefins
Feng, Cheng-Tao
Zhu, Hui-Zhi
Li, Zhong
Luo, Zaigang
Wu, Song-Song
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TETRAHEDRON LETTERS, 2016, 57 (07) : 800 - 803
[3] Synthesis of 3-acylindoles via decarboxylative cross-coupling reaction of free (N-H) indoles with α-oxocarboxylic acids
Gu, Li-Jun
Liu, Ji-Yan
Zhang, Li-Zhu
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CHINESE CHEMICAL LETTERS, 2014, 25 (01) : 90 - 92
[4] Copper-catalyzed decarboxylative C3-acylation of free (N-H) indoles with α-oxocarboxylic acids
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Wang, Shaoyan
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Chen, Xichao
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[5] Synthesis of 3-Acylindoles by Palladium-Catalyzed Acylation of Free (N-H) Indoles with Nitriles
Jiang, Tao-Shan
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[6] 3-Acylindoles via palladium-catalyzed regioselective arylation of electron-rich olefins with indoles
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Xue, Dong
Lu, Wei
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RSC ADVANCES, 2013, 3 (29) : 11463 - 11466
[7] Collective Synthesis of 3-Acylindoles, Indole-3-carboxylic Esters, Indole-3-sulfinic Acids, and 3-(Methylsulfonyl)indoles from Free (N-H) Indoles via Common N-Indolyl Triethylborate
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ORGANIC LETTERS, 2016, 18 (15) : 3918 - 3921
[8] Palladium-catalyzed decarboxylative C3-acylation of benzofurans and benzothiophenes with α-oxocarboxylic acids via direct sp2 C-H bond activation
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Li, Fei-Long
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TETRAHEDRON, 2015, 71 (08) : 1269 - 1275
[9] Bronsted acidic ionic liquid-promoted direct C3-acylation of N-unsubstituted indoles with acid anhydrides under microwave irradiation
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RSC ADVANCES, 2017, 7 (86) : 54399 - 54406
[10] A highly efficient route to C-3 alkyl-substituted indoles via a metal-free transfer hydrogenation
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Feng, Huan-Xi
Li, Zhi-Long
Cai, Pin-Wen
Liu, Yan-Kai
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TETRAHEDRON LETTERS, 2014, 55 (28) : 3774 - 3776

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