Visible Light Promoted Synthesis of Indoles by Single Photosensitizer under Aerobic Conditions

被引：52

作者：

Liu, Wen-Qiang ^{[1
,2
]}

Lei, Tao ^{[1
,2
]}

Song, Zi-Qi ^{[1
,2
]}

Yang, Xiu-Long ^{[1
,2
]}

Wu, Cheng-Juan ^{[1
,2
]}

Jiang, Xin ^{[1
,2
]}

Chen, Bin ^{[1
,2
]}

Tung, Chen-Ho ^{[1
,2
]}

Wu, Li-Zhu ^{[1
,2
]}

机构：

[1] Chinese Acad Sci, Tech Inst Phys & Chem, Key Lab Photochem Convers & Optoelect Mat, Beijing 100190, Peoples R China

[2] Univ Chinese Acad Sci, Beijing 100049, Peoples R China

来源：

ORGANIC LETTERS | 2017年 / 19卷 / 12期

基金：

中国国家自然科学基金;

关键词：

N-ARYL ENAMINES; C-H ACTIVATION; ASSISTED INTRAMOLECULAR AMINATION; DEHYDROGENATIVE COUPLING REACTION; NONREARRANGED MONOTERPENOID UNIT; CATALYZED CASCADE PROCESS; PHOTOREDOX CATALYSIS; INTERNAL ALKYNES; BOND FORMATION; METAL-FREE;

D O I：

10.1021/acs.orglett.7b01367

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The construction of substituted indole skeletons is always an important concern of synthetic chemists because of its prevalent structure found in natural products and biological molecules. Here, we succeeded in preparing indoles and their derivatives from a wide variety of simple enamines via - radical cyclization only with catalytic amounts of an iridium(III) photosensitizer (PS) in DMSO solution under air atmosphere. The mechanistic investigation suggests that the reaction involves a radical course to accomplish the conversion of enamines to indoles under visible light irradiation.

引用

页码：3251 / 3254

页数：4

共 53 条

[1] Annulation of internal alkynes through a hydroamination/aza-Heck reaction sequence for the regioselective synthesis of indoles [J].

Ackermann, Lutz ;

Sandmann, Rene ;

Villar, Amparo ;

Kaspar, Ludwig T. .

TETRAHEDRON, 2008, 64 (05) :769-777

[2] Cationic Ruthenium(II) Catalysts for Oxidative C-H/N-H Bond Functionalizations of Anilines with Removable Directing Group: Synthesis of Indoles in Water [J].

Ackermann, Lutz ;

Lygin, Alexander V. .

ORGANIC LETTERS, 2012, 14 (03) :764-767

[3] Modular Synthesis of Indoles from Imines and o-Dihaloarenes or o-Chlorosulfonates by a Pd-Catalyzed Cascade Process [J].

Barluenga, Jose ;

Jimenez-Aquino, Agustin ;

Aznar, Fernando ;

Valdes, Carlos .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (11) :4031-4041

[4] MECHANISM OF RADICAL PRODUCTION FROM THE REACTION OF CYTOCHROME-C WITH ORGANIC HYDROPEROXIDES - AN ESR SPIN-TRAPPING INVESTIGATION [J].

BARR, DP ;

MASON, RP .

JOURNAL OF BIOLOGICAL CHEMISTRY, 1995, 270 (21) :12709-12716

[5] Copper-Catalyzed C-C Bond Formation through C-H Functionalization: Synthesis of Multisubstituted Indoles from N-Aryl Enaminones [J].

Bernini, Roberta ;

Fabrizi, Giancarlo ;

Sferrazza, Alessio ;

Cacchi, Sandro .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (43) :8078-8081

[6] Synthesis and functionalization of Indoles through palladium-catalyzed reactions [J].

Cacchi, S ;

Fabrizi, G .

CHEMICAL REVIEWS, 2005, 105 (07) :2873-2920

[7] A new synthesis of indoles via intramolecular cyclization of o-alkynyl N,N-dialkylanilines promoted by KOt-Su/DMSO [J].

Chen, Yan-yan ;

Chen, Jia-hua ;

Zhang, Niu-niu ;

Ye, Lin-miao ;

Zhang, Xue-jing ;

Yan, Ming .

TETRAHEDRON LETTERS, 2015, 56 (02) :478-481

[8] Regioselective Pd-catalyzed indolization of 2-bromoanilines with internal alkynes using phosphine-free ligands [J].

Cui, Xin ;

Li, Juan ;

Fu, Yao ;

Liu, Lei ;

Guo, Qing-Xiang .

TETRAHEDRON LETTERS, 2008, 49 (21) :3458-3462

[9] Characterization of the high-resolution ESR spectra of superoxide radical adducts of 5-(diethoxyphosphoryl)-5-methyl-1-pyrroline N-oxide (DEPMPO) and 5,5-dimethyl-1-pyrroline N-oxide (DMPO).: Analysis of conformational exchange [J].

Dikalov, S ;

Jiang, JJ ;

Mason, RP .

FREE RADICAL RESEARCH, 2005, 39 (08) :825-836

[10] Synthesis of N-substituted indole derivatives via PIFA-mediated intramolecular cyclization [J].

Du, Yunfei ;

Liu, Renhe ;

Linn, Gregory ;

Zhao, Kang .

ORGANIC LETTERS, 2006, 8 (26) :5919-5922

← 1 2 3 4 5 6 →