Visible light-induced carbonylation of indoles with arylsulfonyl chlorides and CO

被引：30

作者：

Li, Xiangguang ^{[1
,2
]}

Liang, Deqiang ^{[1
,2
]}

Huang, Wenzhong ^{[1
,2
]}

Zhou, Hongfu ^{[1
]}

Li, Zhao ^{[1
]}

Wang, Baoling ^{[1
,2
]}

Ma, Yinhai ^{[1
]}

Wang, Hai ^{[2
]}

机构：

[1] Kunming Univ, Dept Chem Sci & Technol, Kunming 650214, Peoples R China

[2] Kunming Univ, Key Lab Yunnan Prov Higher Educ Inst Organ Optoel, Kunming 650214, Peoples R China

来源：

TETRAHEDRON | 2016年 / 72卷 / 51期

基金：

中国国家自然科学基金;

关键词：

Indol-3-yl aryl ketones; Carbonylation; Arylsulfonyl chlorides; Indoles; Visible light photocatalysis; PALLADIUM-CATALYZED CARBONYLATION; METAL-FREE; PHOTOREDOX CATALYSIS; ARYL; ROUTE; DERIVATIVES; ACYLATION; EFFICIENT; KETONES; ACCESS;

D O I：

10.1016/j.tet.2016.11.009

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel and simple strategy for the visible light-induced efficient synthesis of indol-3-yl aryl ketones from readily available arylsulfonyl chlorides and indoles with CO at room temperature was developed. This metal-free protocol has good functional group tolerance and avoids the use of transition-metal catalysts, additives, and alkaline or acidic reaction medium. (C) 2016 Elsevier Ltd. All rights reserved.

引用

页码：8442 / 8448

页数：7

共 55 条

[11] ZrCl4-Mediated Regio- and Chemoselective Friedel-Crafts Acylation of Indole [J].

Guchhait, Sankar K. ;

Kashyap, Maneesh ;

Kamble, Harshad .

JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (11) :4753-4758

[12] Metal-Free, Room-Temperature, Radical Alkoxycarbonylation of Aryldiazonium Salts through Visible-Light Photoredox Catalysis [J].

Guo, Wei ;

Lu, Liang-Qiu ;

Wang, Yue ;

Wang, Ya-Ni ;

Chen, Jia-Rong ;

Xiao, Wen-Jing .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (07) :2265-2269

[13] Synthetic applications of eosin Y in photoredox catalysis [J].

Hari, Durga Prasad ;

Koenig, Burkhard .

CHEMICAL COMMUNICATIONS, 2014, 50 (51) :6688-6699

[14] Metal-Free, Visible-Light-Mediated Direct C-H Arylation of Heteroarenes with Aryl Diazonium Salts [J].

Hari, Durga Prasad ;

Schroll, Peter ;

Koenig, Burkhard .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (06) :2958-2961

[15] Highly Regioselective α-Arylation of Coumarins via Palladium-Catalyzed C-H Activation/Desulfitative Coupling [J].

Jafarpour, Farnaz ;

Olia, Mina Barzegar Amiri ;

Hazrati, Hamideh .

ADVANCED SYNTHESIS & CATALYSIS, 2013, 355 (17) :3407-3412

[16] Rh(III)-Catalyzed C-H Amidation of Indoles with Isocyanates [J].

Jeong, Taejoo ;

Han, Sangil ;

Mishra, Neeraj Kumar ;

Sharma, Satyasheel ;

Lee, Seok-Yong ;

Oh, Joa Sub ;

Kwak, Jong Hwan ;

Jung, Young Hoon ;

Kim, In Su .

JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (14) :7243-7250

[17] Palladium-Catalysed Direct Desulfitative Arylation of Pyrroles using Benzenesulfonyl Chlorides as Alternative Coupling Partners [J].

Jin, Rongwei ;

Yuan, Kedong ;

Chatelain, Emmanuelle ;

Soule, Jean-Francois ;

Doucet, Henri .

ADVANCED SYNTHESIS & CATALYSIS, 2014, 356 (18) :3831-3841

[18] BPR0L075, a novel synthetic indole compound with antimitotic activity in human cancer cells, exerts effective antitumoral activity in vivo [J].

Kuo, CC ;

Hsieh, HP ;

Pan, WY ;

Chen, CP ;

Lion, JP ;

Lee, SJ ;

Chang, YL ;

Chen, LT ;

Chen, CT ;

Chang, JY .

CANCER RESEARCH, 2004, 64 (13) :4621-4628

[19] Pd(II)-Catalyzed Decarboxylative Cross-Coupling of Potassium Aryltrifluoroborates with α-Oxocarboxylic Acids at Room Temperature [J].

Li, Mingzong ;

Wang, Cong ;

Ge, Haibo .

ORGANIC LETTERS, 2011, 13 (08) :2062-2064

[20] Efficient synthetic route to bisaryl ketones via copper-catalyzed C-C triple bonds cleavage [J].

Li, Xiangguang ;

Huang, Wenzhong ;

Liang, Deqiang ;

Yuan, Lin ;

Ma, Yinhai ;

Gu, Lijun .

TETRAHEDRON, 2015, 71 (07) :1045-1049

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