Synthesis of 1-Substituted 2-(Trifluoromethyl)indoles via a Palladium-Catalyzed Double Amination Reaction

被引：22

作者：

Dong, Shu-Xiang ^{[1
]}

Zhang, Xing-Guo ^{[1
,2
]}

Liu, Qiong ^{[1
]}

Tang, Ri-Yuan ^{[1
]}

Zhong, Ping ^{[1
]}

Li, Jin-Heng ^{[1
,2
]}

机构：

[1] Wenzhou Univ, Coll Chem & Mat Engn, Wenzhou 325027, Peoples R China

[2] Hunan Normal Univ, Key Lab Chem Biol & Tradit Chinese Med Res, Changsha 410081, Peoples R China

来源：

SYNTHESIS-STUTTGART | 2010年 / 09期

基金：

中国国家自然科学基金;

关键词：

palladium; double amination; 2-chloro-1-(2-halophenyl)-3,3,3-trifluoroprop-1-enes; 2-(trifluoromethyl)indoles; N BOND FORMATION; BEARING METHOXYCARBONYL; TRIFLUOROMETHYL GROUPS; INDOLE-DERIVATIVES; INTERNAL ALKYNES; FLUORINE; ANNULATION; CHEMISTRY; ALKENYL; AMINES;

D O I：

10.1055/s-0029-1218686

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new, selective protocol for the synthesis of 1-substituted 2-(trifluoromethyl)indoles has been developed by palladium-catalyzed double amination reaction of 2-chloro-1-(2-halophenyl)3,3,3-trifluoroprop-1-enes with primary amines. This route allows the formation of two C-N bonds in one pot from the reaction between 2-chloro-1-(2-halophenyl)-3,3,3-trifluoroprop-1-enes and primary amines using the Pd(2)(dba)(3)/L4/t-BuONa system.

引用

页码：1521 / 1525

页数：5

共 43 条

[11] PRACTICAL WAYS FROM ALDEHYDES TO 2-CHLORO-1,1,1-TRIFLUORO-2-ALKENES AND "2-CHLORO-1,1-DIFLUORO-1-ALKEN-3-OLS [J].

FUJITA, M ;

HIYAMA, T .

TETRAHEDRON LETTERS, 1986, 27 (31) :3655-3658

[12] Synthesis and antitumor activity of novel cyclopropapyrroloindole (CPI) derivatives bearing methoxycarbonyl and trifluoromethyl groups [J].

Fukuda, Y ;

Furuta, H ;

Shiga, F ;

Oomori, Y ;

Kusama, Y ;

Ebisu, H ;

Terashima, S .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1997, 7 (13) :1683-1688

[13] Novel cyclopropapyrroloindole derivative (AT-3510) bearing methoxycarbonyl and trifluoromethyl groups [J].

Fukuda, Y ;

Furuta, H ;

Kusama, Y ;

Ebisu, H ;

Oomori, Y ;

Terashima, S .

JOURNAL OF MEDICINAL CHEMISTRY, 1999, 42 (08) :1448-1458

[14]

FURSTNER A, 1995, J AM CHEM SOC, V117, P4468

[15] Grignard cyclization reaction of fluorinated N-arylimidoyl chlorides:: A novel and facile access to 2-fluoroalkyl indoles [J].

Ge, Fenglian ;

Wang, Zengxue ;

Wan, Wen ;

Hao, Jian .

SYNLETT, 2007, (03) :447-450

[16] Tandem copper-catalysed aryl and alkenyl amination reactions: the synthesis of N-functionalised indoles [J].

Hodgkinson, Roy C. ;

Schulz, Jurgen ;

Willis, Michael C. .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2009, 7 (03) :432-434

[17] 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

[18] A novel approach to fluoro-containing alkenes [J].

Korotchenko, VN ;

Shastin, AV ;

Nenajdenko, VG ;

Balenkova, ES .

TETRAHEDRON, 2001, 57 (35) :7519-7527

[19] Synthesis of 2,3-disubstituted indoles via palladium-catalyzed annulation of internal alkynes [J].

Larock, RC ;

Yum, EK ;

Refvik, MD .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (22) :7652-7662

[20] Synthesis of indoles and quinolones by sequential Wittig and Heck reactions [J].

Latham, EJ ;

Stanforth, SP .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1997, (14) :2059-2063

← 1 2 3 4 5 →