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

被引：53

作者：

Djakovitch, Laurent ^{[1
]}

Rouge, Pascal ^{[1
]}

机构：

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

来源：

JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL | 2007年 / 273卷 / 1-2期

关键词：

3-vinyl indoles; oxidative coupling; palladium-copper catalysts; zeolites;

D O I：

10.1016/j.molcata.2007.04.011

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

A new palladium/copper catalytic procedure for the C-3-alkenylation of free NH-indoles is reported. Using homogeneous or heterogeneous hetero-bimetallic [Pd/Cu] -catalysts under mild reaction conditions (10 mol% Pd-catalyst and 10 mol% Cu-catalyst, 70 degrees C, air), substituted indoles are fully (58-82% isolated yields) and selectively (75-100% selectivity) converted to the expected 2-substituted-3-vinyl indoles. (C) 2007 Elsevier B.V. All rights reserved.

引用

收藏

页码：230 / 239

页数：10

相关论文

共 59 条

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

Ackermann, L .

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

[2]

[Anonymous], 1996, PALLADIUM REAGENTS C

[3]

ARCADI A, 1992, TETRAHEDRON LETT, V33, P3915

[4]

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

[5] 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

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

Cacchi, S ;

Fabrizi, G .

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

[7] 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

[8] Nitrogen-containing heterocycles via palladium-catalyzed reaction of alkynes with organic halides or triflates [J].

Cacchi, S ;

Fabrizi, G ;

Parisi, LM .

HETEROCYCLES, 2002, 58 :667-682

[9] Directed palladation: fine tuning permits the catalytic 2-alkenylation of indoles [J].

Capito, E ;

Brown, JM ;

Ricci, A .

CHEMICAL COMMUNICATIONS, 2005, (14) :1854-1856

[10] Aryl transfer between Pd(II) centers or Pd(IV) intermediates in Pd-catalyzed domino reactions [J].

Cárdenas, DJ ;

Martín-Matute, B ;

Echavarren, AM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (15) :5033-5040

← 1 2 3 4 5 6 →