Copper-catalyzed synthesis of benzocarbazoles via α-C-arylation of ketones

被引：47

作者：

Xie, Ruilong ^{[1
,2
]}

Ling, Yun ^{[2
]}

Fu, Hua ^{[1
,3
]}

机构：

[1] Tsinghua Univ, Dept Chem, Key Lab Bioorgan Phosphorus Chem & Chem Biol, Minist Educ, Beijing 100084, Peoples R China

[2] China Agr Univ, Key Lab Pesticide Chem & Applicat, Dept Appl Chem, Coll Sci,Minist Agr, Beijing 100193, Peoples R China

[3] Tsinghua Univ, Grad Sch Shenzhen, Key Lab Chem Biol Guangdong Prov, Shenzhen 518057, Peoples R China

来源：

CHEMICAL COMMUNICATIONS | 2012年 / 48卷 / 100期

基金：

中国国家自然科学基金;

关键词：

COUPLING REACTIONS; ARYL BROMIDES; PALLADIUM; EFFICIENT; DERIVATIVES; COMPLEXES; LIGANDS; ULLMANN; VERSATILE; HALIDES;

D O I：

10.1039/c2cc36403d

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A simple and efficient copper-catalyzed method for the synthesis of 11H-benzo[a]carbazoles has been developed. The protocol uses readily available substituted 2-(2-bromophenyl)-1H-indoles and ketones as starting materials and an inexpensive catalyst system. The corresponding 11H-benzo[a] carbazoles were obtained in moderate to excellent yields.

引用

收藏

页码：12210 / 12212

页数：3

相关论文

共 49 条

[1] Palladium complexes of 1,3,5,7-tetramethyl-2,4,8-trioxa-6-phenyl-6-phosphaadamantane:: Synthesis, crystal structure and use in the Suzuki and Sonogashira reactions and the α-arylation of ketones [J].

Adjabeng, G ;

Brenstrum, T ;

Frampton, CS ;

Robertson, AJ ;

Hillhouse, J ;

McNulty, J ;

Capretta, A .

JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (15) :5082-5086

[2]

Beight D. W., 2002, US patent, Patent No. [WO 2002050034, 2002050034]

[3]

Beight D. W., 2002, CHEM ABSTR, V137, P47114

[4] Copper in cross-coupling reactions - The post-Ullmann chemistry [J].

Beletskaya, IP ;

Cheprakov, AV .

COORDINATION CHEMISTRY REVIEWS, 2004, 248 (21-24) :2337-2364

[5] Transition Metal-Catalyzed Direct Arylation of Substrates with Activated sp3-Hybridized C-H Bonds and Some of Their Synthetic Equivalents with Aryl Halides and Pseudohalides [J].

Bellina, Fabio ;

Rossi, Renzo .

CHEMICAL REVIEWS, 2010, 110 (02) :1082-1146

[6] Combined directed ortho and remote metalation -: Cross-coupling strategies.: General method for benzo[a]carbazoles and the synthesis of an unnamed indolo[2,3-a]carbazole alkaloid [J].

Cai, XW ;

Snieckus, V .

ORGANIC LETTERS, 2004, 6 (14) :2293-2295

[7] An advantageous route to oxcarbazepine (Trileptal) based on palladium-catalyzed arylations free of transmetallating agents [J].

Carril, M ;

SanMartin, R ;

Churruca, F ;

Tellitu, I ;

Domínguez, E .

ORGANIC LETTERS, 2005, 7 (22) :4787-4789

[8] Elaboration of 2-(trifluoromethyl)indoles via a cascade coupling/condensation/deacylation process [J].

Chen, Yu ;

Wang, Yuji ;

Sun, Zheming ;

Ma, Dawei .

ORGANIC LETTERS, 2008, 10 (04) :625-628

[9] Facile access to polysubstituted Indoles via a cascade Cu-catalyzed arylation - Condensation process [J].

Chen, Yu ;

Xie, Xiaoan ;

Ma, Dawei .

JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (24) :9329-9334

[10] Highly efficient and mild copper-catalyzed N- and C-arylations with aryl bromides and iodides [J].

Cristau, HJ ;

Cellier, PP ;

Spindler, JF ;

Taillefer, M .

CHEMISTRY-A EUROPEAN JOURNAL, 2004, 10 (22) :5607-5622

← 1 2 3 4 5 →