2,3-disubstituted indoles through the palladium-catalyzed reaction of aryl chlorides with o-alkynyltrifluoroacetanilides

被引：70

作者：

Cacchi, Sandro ^{[1
]}

Fabrizi, Giancarlo ^{[1
]}

Goggiamani, Antonella ^{[1
]}

机构：

[1] Univ Roma La Sapienza, Dipartimento Studi Chim & Tecnol Sostanze Biologi, I-00185 Rome, Italy

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2006年 / 348卷 / 10-11期

关键词：

alkynes; aminopalladation-reductive elimination; cyclization; indoles; palladium;

D O I：

10.1002/adsc.200606060

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

2,3-Disubstituted indoles can be prepared in moderate to excellent yields by reacting readily available o-alkynyltrifluoroacetanilides with aryl chlorides in MeCN at 120 degrees C in the presence of Pd-2(dba)(3) and Xphos.

引用

页码：1301 / 1305

页数：5

共 12 条

[1] Palladium-catalyzed reaction of o-alkynyltrifluoroacetanilides with 1-bromoalkynes.: An approach to 2-substituted 3-alkynylindoles and 2-substituted 3-acylindoles [J].

Arcadi, A ;

Cacchi, S ;

Fabrizi, G ;

Marinelli, F ;

Parisi, LM .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (16) :6213-6217

[2] Catalysts for Suzuki-Miyaura coupling processes: Scope and studies of the effect of ligand structure [J].

Barder, TE ;

Walker, SD ;

Martinelli, JR ;

Buchwald, SL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (13) :4685-4696

[3]

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

[4] Synthesis and functionalization of Indoles through palladium-catalyzed reactions [J].

Cacchi, S ;

Fabrizi, G .

CHEMICAL REVIEWS, 2005, 105 (07) :2873-2920

[5] 2-substituted 3-aryl- and 3-heteroarylindoles by the palladium-catalyzed reaction of o-trifluoroacetanilides with aryl bromides and triflates [J].

Cacchi, S ;

Fabrizi, G ;

Lamba, D ;

Marinelli, F ;

Parisi, LM .

SYNTHESIS-STUTTGART, 2003, (05) :728-734

[6] Palladium-catalyzed cyclization of o-alkynyltrifluoroacetanilides with allyl esters. A regioselective synthesis of 3-allylindoles [J].

Cacchi, S ;

Fabrizi, G ;

Pace, P .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (04) :1001-1011

[7] Expanding Pd-catalyzed C-N bond-forming processes: The first amidation of aryl sulfonates, aqueous amination, and complementarity with Cu-catalyzed reactions [J].

Huang, XH ;

Anderson, KW ;

Zim, D ;

Jiang, L ;

Klapars, A ;

Buchwald, SL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (22) :6653-6655

[8]

Littke AF, 2002, ANGEW CHEM INT EDIT, V41, P4176, DOI 10.1002/1521-3773(20021115)41:22<4176::AID-ANIE4176>3.0.CO

[9]

2-U

[10] Air-stable trialkylphosphonium salts: Simple, practical, and versatile replacements for air-sensitive trialkylphosphines. Applications in stoichiometric and catalytic processes [J].

Netherton, MR ;

Fu, GC .

ORGANIC LETTERS, 2001, 3 (26) :4295-4298

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