Aerobic Transition-Metal-Free Visible-Light Photoredox Indole C-3 Formylation Reaction

被引：142
作者：
Li, Xiang [1 ]
Gu, Xiangyong [1 ]
Li, Yongjuan [1 ]
Li, Pixu [1 ]
机构：
[1] Soochow Univ, Coll Chem Chem Engn & Mat Sci, Key Lab Organ Synth Jiangsu Prov, Suzhou 215123, Jiangsu, Peoples R China
来源：
ACS CATALYSIS | 2014年 / 4卷 / 06期
关键词：
aerobic oxidation; visible light photoredox; indole formylation; Rose Bengal; transition-metal-free; C-H; ARYLATION; CATALYSIS; OXIDATION; FUNCTIONALIZATION; C3-FORMYLATION; PHOTOCATALYSIS;
D O I：
10.1021/cs5005129
中图分类号：
O64 [物理化学（理论化学）、化学物理学];
学科分类号：
070304 ; 081704 ;
摘要：
An aerobic visible-light-promoted indole C-3 formylation reaction catalyzed by Rose Bengal has been developed. This transition-metal-free process employs molecular oxygen as the terminal oxidant and uses TMEDA as the one-carbon source through C-N bond cleavage. The reaction is compatible with a variety of functional groups.
引用
收藏
页码：1897 / 1900
页数：4
相关论文
共 42 条
[1]   ESTIMATION OF EXCITED-STATE REDOX POTENTIALS BY ELECTRON-TRANSFER QUENCHING - APPLICATION OF ELECTRON-TRANSFER THEORY TO EXCITED-STATE REDOX PROCESSES [J].
BOCK, CR ;
CONNOR, JA ;
GUTIERREZ, AR ;
MEYER, TJ ;
WHITTEN, DG ;
SULLIVAN, BP ;
NAGLE, JK .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1979, 101 (17) :4815-4824
[2]   Visible-Light-Promoted C-C Bond Cleavage: Photocatalytic Generation of Iminium Ions and Amino Radicals [J].
Cai, Shunyou ;
Zhao, Xinyang ;
Wang, Xinbo ;
Liu, Qisong ;
Li, Zigang ;
Wang, David Zhigang .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (32) :8050-8053
[3]   The Copper-Catalyzed C-3-Formylation of Indole C-H Bonds using Tertiary Amines and Molecular Oxygen [J].
Chen, Jianbin ;
Liu, Bin ;
Liu, Dongfang ;
Liu, Shan ;
Cheng, Jiang .
ADVANCED SYNTHESIS & CATALYSIS, 2012, 354 (13) :2438-2442
[4]   Visible light-induced 3-sulfenylation of N-methylindoles with arylsulfonyl chlorides [J].
Chen, Min ;
Huang, Zhi-Tang ;
Zheng, Qi-Yu .
CHEMICAL COMMUNICATIONS, 2012, 48 (95) :11686-11688
[5]   Friedel-Crafts Amidoalkylation via Thermolysis and Oxidative Photocatalysis [J].
Dai, Chunhui ;
Meschini, Francesco ;
Narayanam, Jagan M. R. ;
Stephenson, Corey R. J. .
JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (09) :4425-4431
[6]   The ammonium-promoted formylation of indoles by DMSO and H2O [J].
Fei, Haiyang ;
Yu, Jintao ;
Jiang, Yan ;
Guo, Huan ;
Cheng, Jiang .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2013, 11 (41) :7092-7095
[7]   Functionally Diverse Nucleophilic Trapping of Iminium Intermediates Generated Utilizing Visible Light [J].
Freeman, David B. ;
Furst, Laura ;
Condie, Allison G. ;
Stephenson, Corey R. J. .
ORGANIC LETTERS, 2012, 14 (01) :94-97
[8]   Selective photocatalytic reactions with organic photocatalysts [J].
Fukuzumi, Shunichi ;
Ohkubo, Kei .
CHEMICAL SCIENCE, 2013, 4 (02) :561-574
[9]   A simple metal-free catalytic sulfoxidation under visible light and air [J].
Gu, Xiangyong ;
Li, Xiang ;
Chai, Yahong ;
Yang, Qi ;
Li, Pixu ;
Yao, Yingming .
GREEN CHEMISTRY, 2013, 15 (02) :357-361
[10]   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
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