A practical mild, one-pot, regiospecific synthesis of 2,3-disubstituted indoles via consecutive Sonogashira and Cacchi reactions

被引：129

作者：

Lu, Bruce Z. ^{[1
]}

Zhao, Wenyi ^{[1
]}

Wei, Han-Xun ^{[1
]}

Dufour, Marine ^{[1
]}

Farina, Vittorio ^{[1
]}

Senanayake, Chris H. ^{[1
]}

机构：

[1] Boehringer Ingelheim Pharmaceut Inc, Dept Chem Dev, Richmond, VA 23219 USA

来源：

ORGANIC LETTERS | 2006年 / 8卷 / 15期

关键词：

COPPER-FREE; COUPLING REACTION; TERMINAL ALKYNES; ARYL BROMIDES; PALLADIUM; EFFICIENT; VINYL; HALIDES; CYCLIZATION; 1-ALKYNES;

D O I：

10.1021/ol061136q

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A practical one-pot, regiospecific three-component process for the synthesis of 2,3-disubstituted indoles was developed via consecutive Pd-catalyzed Sonogashira coupling, amidopalladation, and reductive elimination.

引用

页码：3271 / 3274

页数：4

共 29 条

[1] AN EFFICIENT PALLADIUM-CATALYZED REACTION OF VINYL AND ARYL HALIDES OR TRIFLATES WITH TERMINAL ALKYNES [J].

ALAMI, M ;

FERRI, F ;

LINSTRUMELLE, G .

TETRAHEDRON LETTERS, 1993, 34 (40) :6403-6406

[2] A copper- and amine-free Sonogashira-type coupling procedure catalyzed by oxime palladacycles [J].

Alonso, DA ;

Nájera, C ;

Pacheco, MC .

TETRAHEDRON LETTERS, 2002, 43 (51) :9365-9368

[3]

ARCADI A, 1992, TETRAHEDRON LETT, V33, P3915

[4]

Battistuzzi G, 2002, EUR J ORG CHEM, V2002, P2671

[5]

Böhm VPW, 2000, EUR J ORG CHEM, V2000, P3679, DOI 10.1002/1099-0690(200011)2000:22<3679::AID-EJOC3679>3.0.CO

[6]

2-X

[7]

Brandsma L., 1998, APPL TRANSITION META

[8] 2-aryl and 2-heteroaryl indoles from 1-alkynes and o-lodotrifluoroacetanilide through a domino copper-catalyzed coupling-cyclization process [J].

Cacchi, S ;

Fabrizi, G ;

Parisi, LM .

ORGANIC LETTERS, 2003, 5 (21) :3843-3846

[9]

Faulkner DJ, 1999, NAT PROD REP, V16, P155

[10]

Fischer E., 1883, CHEM BER, V16, P6

← 1 2 3 →