Palladium-catalyzed three-component synthesis of 3-(diarylmethylene)oxindoles through a domino Sonagashira/carbopalladation/C-H activation/C-C bond-forming sequence

被引：190

作者：

Pinto, Artur ^{[1
]}

Neuville, Luc ^{[1
]}

Zhu, Jieping ^{[1
]}

机构：

[1] CNRS, Inst Chim Subst Nat, F-91198 Gif Sur Yvette, France

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2007年 / 46卷 / 18期

关键词：

C-H activation; domino reactions; multicomponent reactions; nitrogen heterocycles; palladium;

D O I：

10.1002/anie.200605192

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Chemical Equation Presented) 3-3-1 Formation: [Pd(PPh3) 4]/Cul serves as an efficient catalyst for the reaction of three readily available starting materials to give 3-(diarylmethylene)indolin-2-ones 3 through a sequence of intermolecular Sonagashira reaction/intermolecular carbopalladation/C-H activation/C-C bond formation (see scheme). Three C-C bonds are thereby formed as a result of three distinct catalytic cycles with one catalyst. DMF = N,N-dimethylformamide. © 2007 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：3291 / 3295

页数：5

共 78 条

[1] Two birds with one metallic stone: Single-pot catalysis of fundamentally different transformations [J].

Ajamian, A ;

Gleason, JL .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (29) :3754-3760

[2]

Ajamian A., 2004, ANGEW CHEM, V116, P3842

[3] 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

[4] Highly satisfactory procedures for the Pd-catalyzed cross coupling of aryl electrophiles with in situ generated alkynylzinc derivatives [J].

Anastasia, L ;

Negishi, E .

ORGANIC LETTERS, 2001, 3 (20) :3111-3113

[5] Antitumor activity of substituted E-3-(3,4,5-trimethoxybenzylidene)-1,3-dihydroindol-2-ones [J].

Andreani, Aldo ;

Burnelli, Silvia ;

Granaiola, Massimiliano ;

Leoni, Alberto ;

Locatelli, Alessandra ;

Morigi, Rita ;

Rambaldi, Mirella ;

Varoli, Lucilla ;

Kunkel, Mark W. .

JOURNAL OF MEDICINAL CHEMISTRY, 2006, 49 (23) :6922-6924

[6] Sonogashira cross-coupling reaction of 3-iodoindazoles with various terminal alkynes: a mild and flexible strategy to design 2-aza tryptamines [J].

Arnautu, A ;

Collot, V ;

Ros, JC ;

Alayrac, C ;

Witulski, B ;

Rault, S .

TETRAHEDRON LETTERS, 2002, 43 (15) :2695-2697

[7] Pd-assisted multicomponent synthesis of heterocycles [J].

Balme, G ;

Bossharth, E ;

Monteiro, N .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2003, 2003 (21) :4101-4111

[8]

Banfi L., 2005, ORG REACTIONS, V65, P1, DOI [10.1002/0471264180.or065.01, DOI 10.1002/0471264180.0R065.01]

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

Cacchi, S ;

Fabrizi, G .

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

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

Campeau, LC ;

Fagnou, K .

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

← 1 2 3 4 5 6 7 8 →