Synthesis of 2-trifluoromethyl indoles via visible-light induced intramolecular radical cyclization

被引：28

作者：

Dong, Xichang ^{[1
]}

Hu, Yumin ^{[1
]}

Xiao, Tiebo ^{[1
]}

Zhou, Lei ^{[1
]}

机构：

[1] Sun Yat Sen Univ, Sch Chem & Chem Engn, Guangzhou 510275, Guangdong, Peoples R China

来源：

RSC ADVANCES | 2015年 / 5卷 / 49期

基金：

中国国家自然科学基金;

关键词：

REGIOSELECTIVE SYNTHESIS; BEARING METHOXYCARBONYL; OXIDATIVE CYCLIZATION; PHOTOREDOX CATALYSIS; ELECTRON-TRANSFER; METAL-FREE; GENERATION; TRIFLUOROMETHYLATION; CATIONS; ALKYNES;

D O I：

10.1039/c5ra05967d

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A visible-light induced intramolecular radical cyclization of N-[2(alkynyl)phenyl] trifluoroacetimidoyl chlorides is described. The reaction allows the rapid construction of diverse 2-trifluoromethyl-3-acylindoles in a sequential C-C and C-O bond formation process under mild conditions.

引用

页码：39625 / 39629

页数：5

共 51 条

[21]

Kirsch P., 2004, MODERN FLUOROORGANIC

[22] A facile regiocontrol in the palladium-catalyzed annulation of fluorine-containing internal alkynes with variously substituted 2-iodoanilines: A new regioselective synthesis of 2-or 3-fluoroalkylated indole derivatives [J].

Konno, T ;

Chae, J ;

Ishihara, T ;

Yamanaka, H .

JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (24) :8258-8265

[23] Rhenium-Catalyzed Trifluoromethylation of Arenes and Heteroarenes by Hypervalent Iodine Reagents [J].

Mejia, Esteban ;

Togni, Antonio .

ACS CATALYSIS, 2012, 2 (04) :521-527

[24] α-Trifluoromethyl-β-aryl enamines in the synthesis of trifluoromethylated heterocycles by the Fischer and the Pictet-Spengler reactions [J].

Muzalevskiy, Vasiliy M. ;

Nenajdenko, Valentine G. ;

Shastin, Aleksey V. ;

Balenkova, Elizabeth S. ;

Haufe, Guenter .

TETRAHEDRON, 2009, 65 (36) :7553-7561

[25] Trifluoromethylation of arenes and heteroarenes by means of photoredox catalysis [J].

Nagib, David A. ;

MacMillan, David W. C. .

NATURE, 2011, 480 (7376) :224-228

[26]

Ojima I, 2009, MED CHEM CHEM BIOL

[27] Visible Light Photoredox Catalysis with Transition Metal Complexes: Applications in Organic Synthesis [J].

Prier, Christopher K. ;

Rankic, Danica A. ;

MacMillan, David W. C. .

CHEMICAL REVIEWS, 2013, 113 (07) :5322-5363

[28] Photoredox Catalysis for Organic Syntheses [J].

Reckenthaeler, Melissa ;

Griesbeck, Axel G. .

ADVANCED SYNTHESIS & CATALYSIS, 2013, 355 (14-15) :2727-2744

[29] Photoredox functionalization of C-H bonds adjacent to a nitrogen atom [J].

Shi, Lei ;

Xia, Wujiong .

CHEMICAL SOCIETY REVIEWS, 2012, 41 (23) :7687-7697

[30] Direct C2-trifluoromethylation of indole derivatives catalyzed by copper acetate [J].

Shimizu, Ryo ;

Egami, Hiromichi ;

Nagi, Tatsuya ;

Chae, Jungha ;

Hamashima, Yoshitaka ;

Sodeoka, Mikiko .

TETRAHEDRON LETTERS, 2010, 51 (45) :5947-5949

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