Palladium-Catalyzed Direct Denitrogenative C-3-Arylation of 1H-Indoles with Arylhydrazines using Air as the Oxidant

被引：91

作者：

Chen, Yongxin ^{[1
,2
]}

Guo, Shuaibo ^{[1
,2
]}

Li, Kangning ^{[1
,2
]}

Qu, Jinpeng ^{[1
,2
]}

Yuan, Hua ^{[1
,2
]}

Hua, Qiuru ^{[1
,2
]}

Chen, Baohua ^{[1
,2
]}

机构：

[1] Lanzhou Univ, State Key Lab Appl Organ Chem, Lanzhou 730000, Gansu, Peoples R China

[2] Key Lab Nonferrous Met Chem & Resources Utilizat, Lanzhou 730000, Peoples R China

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2013年 / 355卷 / 04期

基金：

美国国家科学基金会;

关键词：

arylhydrazines; 3-aryl-1H-indoles; CH activation; denitrogenative process; palladium-catalyzed reaction; HECK-TYPE REACTION; C BOND FORMATION; DESULFITATIVE ARYLATION; C-3; ARYLATION; INDOLES; AZOLES; PHENYLHYDRAZINES; PHENYLATION; ALKYLATION; REAGENTS;

D O I：

10.1002/adsc.201200997

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

A novel palladium-catalyzed approach to direct C-3-arylation of 1H-indoles with arylhydrazines using air as the oxidant via CN bond cleavage has been developed. Various substituents are tolerated in this system in moderate to good yields. This reaction could also be compatible with a larger scale. Thus, this strategy using arylhydrazines as arylating reagents provides a powerful method for constructing substituted 3-aryl-1H-indoles.

引用

页码：711 / 715

页数：5

共 57 条

[1]

Ackermann L., 2009, ANGEW CHEM, V121, P9976, DOI DOI 10.1002/ANGE.200902996

[2] Metal-Free Direct Arylations of Indoles and Pyrroles with Diaryliodonium Salts [J].

Ackermann, Lutz ;

Dell'Acqua, Monica ;

Fenner, Sabine ;

Vicente, Ruben ;

Sandmann, Rene .

ORGANIC LETTERS, 2011, 13 (09) :2358-2360

[3] Transition-Metal-Catalyzed Direct Arylation of (Hetero)Arenes by C-H Bond Cleavage [J].

Ackermann, Lutz ;

Vicente, Ruben ;

Kapdi, Anant R. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (52) :9792-9826

[4] Aryl-aryl bond formation by transition-metal-catalyzed direct arylation [J].

Alberico, Dino ;

Scott, Mark E. ;

Lautens, Mark .

CHEMICAL REVIEWS, 2007, 107 (01) :174-238

[5]

[Anonymous], 2004, ANGEW CHEM

[6]

[Anonymous], 2008, ANGEW CHEM INT EDIT

[7] PENTAVALENT ORGANOBISMUTH REAGENTS .3. PHENYLATION OF ENOLS AND OF ENOLATE AND OTHER ANIONS [J].

BARTON, DHR ;

BLAZEJEWSKI, JC ;

CHARPIOT, B ;

FINET, JP ;

MOTHERWELL, WB ;

PAPOULA, MTB ;

STANFORTH, SP .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1985, (12) :2667-2675

[8] COPPER CATALYZED PHENYLATION OF INDOLES BY TRIPHENYLBISMUTH BIS-TRIFLUOROACETATE [J].

BARTON, DHR ;

FINET, JP ;

KHAMSI, J .

TETRAHEDRON LETTERS, 1988, 29 (10) :1115-1118

[9]

Beller M., 2004, TRANSITION METALS OR

[10] Direct palladium-catalyzed C-3 arylation of free (NH)-indoles with aryl bromides under ligandless conditions [J].

Bellina, Fabio ;

Benelli, Francesca ;

Rossi, Renzo .

JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (14) :5529-5535

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