First heterogeneously palladium-catalysed fully selective C3-arylation of free NH-indoles

被引：89

作者：

Cusati, Giuseppe ^{[1
]}

Djakovitch, Laurent ^{[1
]}

机构：

[1] Univ Lyon 1, CNRS, IRCELYON Inst Rech Catalyse & Environm Lyon, UMR 5256, F-69626 Villeurbanne, France

来源：

TETRAHEDRON LETTERS | 2008年 / 49卷 / 16期

关键词：

Indoles; selective C3-arylation; palladium; heterogeneous catalysis;

D O I：

10.1016/j.tetlet.2008.02.130

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A simple heterogeneously palladium-catalysed procedure for the selective C3-arylation of indoles is reported. Under relatively standard reaction conditions (Pd-catalyst, K(2)CO(3), dioxane, reflux), using only 1 mol % [Pd(NH(3))(4)]/NaY as the catalyst, indoles substituted or not at position 2 gave up to 92% conversion (i.e., 85% isolated yield) towards the expected C3-arylated indole. (c) 2008 Elsevier Ltd. All rights reserved.

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页码：2499 / 2502

页数：4

相关论文

共 27 条

[1] General and efficient indole syntheses based on catalytic amination reactions [J].

Ackermann, L .

ORGANIC LETTERS, 2005, 7 (03) :439-442

[2] Palladium- and copper-mediated direct C-2 arylation of azoles - Including free (NH)-imidazole, -benzimidazole and -indole - Under base-free and ligandless conditions [J].

Bellina, F ;

Cauteruccio, S ;

Rossi, R .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2006, 2006 (06) :1379-1382

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

Cacchi, S ;

Fabrizi, G .

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

[4] 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

[5]

Cacchi S, 1997, SYNLETT, P1363

[6]

CLARK RD, 1984, HETEROCYCLES, V22, P195

[7] Room temperature palladium-catalyzed 2-arylation of indoles [J].

Deprez, NR ;

Kalyani, D ;

Krause, A ;

Sanford, MS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (15) :4972-4973

[8] Heck reaction catalyzed by Pd-modified zeolites [J].

Djakovitch, L ;

Koehler, K .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (25) :5990-5999

[9] Selective arylation of 2-substituted indoles towards 1,2-and 2,3-functional indoles directed through the catalytic system [J].

Djakovitch, Laurent ;

Rouge, Pascal ;

Zaidi, Rabah .

CATALYSIS COMMUNICATIONS, 2007, 8 (11) :1561-1566

[10] New homogeneously and heterogeneously [Pd/Cu]-catalysed C3-alkenylation of free NH-indoles [J].

Djakovitch, Laurent ;

Rouge, Pascal .

JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2007, 273 (1-2) :230-239