Silver-Promoted Domino Pd-Catalyzed Amination/Direct Arylation: Access to Polycyclic Heteroaromatics

被引：92

作者：

Bryan, Christopher S. ^{[1
]}

Lautens, Mark ^{[1
]}

机构：

[1] Univ Toronto, Dept Chem, Davenport Labs, Toronto, ON M5S 3H6, Canada

来源：

ORGANIC LETTERS | 2008年 / 10卷 / 20期

基金：

加拿大自然科学与工程研究理事会;

关键词：

D O I：

10.1021/ol801932z

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Novel tetracyclic and pentacyclic indole derivatives can be prepared from readily available gem-dibromovinyl substrates in a single step by means of an efficient Pd-catalyzed domino Buchwald-Hartwig amination/direct arylation reaction. Enhanced reactivity and selectivity are obtained by the addition of silver salts.

引用

页码：4633 / 4636

页数：4

共 39 条

[1] Domino N-H/C-H bond activation: Palladium-catalyzed synthesis of annulated heterocycles using dichloro(hetero)arenes [J].

Ackermann, Lutz ;

Althammer, Andreas .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (10) :1627-1629

[2] 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

[3]

[Anonymous], 2005, HDB C H TRANSFORMATI

[4] Functionalized acenes and heteroacenes for organic electronics [J].

Anthony, John E. .

CHEMICAL REVIEWS, 2006, 106 (12) :5028-5048

[5] A novel catalytic one-pot synthesis of carbazoles via consecutive amination and C-H activation [J].

Bedford, RB ;

Cazin, CSJ .

CHEMICAL COMMUNICATIONS, 2002, (20) :2310-2311

[6] N-H carbazole synthesis from 2-chloroanilines via consecutive amination and C-H activation [J].

Bedford, Robin B. ;

Betham, Michael .

JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (25) :9403-9410

[7] A route to annulated indoles via a palladium-catalyzed tandem alkylation/direct arylation reaction [J].

Bressy, C ;

Alberico, D ;

Lautens, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (38) :13148-13149

[8] Catalytic direct arylation with aryl chlorides, bromides, and iodides: Intramolecular studies leading to new intermolecular reactions [J].

Campeau, LC ;

Parisien, M ;

Jean, A ;

Fagnou, K .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (02) :581-590

[9] Palladium-catalyzed direct arylation of simple arenes in synthesis of biaryl molecules [J].

Campeau, LC ;

Fagnou, K .

CHEMICAL COMMUNICATIONS, 2006, (12) :1253-1264

[10]

Campeau LC, 2007, ALDRICHIM ACTA, V40, P35

← 1 2 3 4 →