Nickel-catalyzed electrochemical arylation of activated olefins

被引：0

作者：

Condon, S ^{[1
]}

Dupré, D ^{[1
]}

Falgayrac, G ^{[1
]}

Nédélec, JY ^{[1
]}

机构：

[1] Univ Paris 12, CNRS, UMR 7582, Lab Electrochim Catalyse & Synth Organ, F-94320 Thiais, France

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2002年 / 2002卷 / 01期

关键词：

addition; catalysis; electrochemistry; nickel; olefins;

D O I：

10.1002/1099-0690(20021)2002:1<105::AID-EJOC105>3.0.CO;2-J

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Nickel-catalyzed electrochemical conjugate additions of substituted aryl bromides to activated olefins under recently optimized reaction conditions are reported. Good to high yields were obtained, whatever the nature of substituents in the meta- and para-positions of the benzene ring. In the ortho-substituted series, yields were good with electron-donating substituents, but low with electron-withdrawing groups. The activation of aryl chlorides and the sequential functionalization of aryl dihalides were also investigated.

引用

页码：105 / 111

页数：7

共 33 条

[11] NEW AROMATIC MUSK ODORANTS - DESIGN AND SYNTHESIS [J].

FEHR, C ;

GALINDO, J ;

HAUBRICHS, R ;

PERRET, R .

HELVETICA CHIMICA ACTA, 1989, 72 (07) :1537-1553

[12] Cross-coupling of chloroarenes with boronic acids using a water-soluble nickel catalyst. [J].

Galland, JC ;

Savignac, M ;

Genêt, JP .

TETRAHEDRON LETTERS, 1999, 40 (12) :2323-2326

[13] Ni(II)-catalyzed cross-coupling between polyfunctional arylzinc derivatives and primary alkyl iodides [J].

Giovannini, R ;

Knochel, P .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (43) :11186-11187

[14] Cobalt bromide as catalyst in electrochemical addition of aryl halides onto activated olefins [J].

Gomes, P ;

Gosmini, C ;

Nédélec, JY ;

Périchon, J .

TETRAHEDRON LETTERS, 2000, 41 (18) :3385-3388

[15]

GOUDIE AC, 1978, J MED CHEM, V21, P1260, DOI 10.1021/jm00210a016

[16] A SYNTHESIS OF FUNCTIONALIZED TRICYCLO[5.2.2.01,5]UNDECENES RELATED TO THE ISOEREMOLACTONE SKELETON [J].

HAGIWARA, H ;

UDA, H .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1986, (04) :629-632

[17] Suzuki-type coupling of chloroarenes with arylboronic acids catalysed by nickel complexes [J].

Indolese, AF .

TETRAHEDRON LETTERS, 1997, 38 (20) :3513-3516

[18] ANTIINFLAMMATORY ACTIVITY OF SOME INDAN-1-CARBOXYLIC ACIDS AND RELATED COMPOUNDS [J].

JUBY, PF ;

PARTYKA, RA ;

HUDYMA, TW ;

GOODWIN, WR .

JOURNAL OF MEDICINAL CHEMISTRY, 1972, 15 (12) :1297-&

[19] REACTIONS OF ARYLAZO ARYL SULFONES WITH ALPHA,BETA-UNSATURATED ESTERS AND KETONES CATALYZED BY PALLADIUM(0) COMPLEX .4. [J].

KAMIGATA, N ;

SATOH, A ;

YOSHIDA, M .

PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 1989, 46 (3-4) :121-129

[20] One-step cross-coupling reaction of functionalized alkyl iodides with aryl halides by the use of an electrochemical method [J].

Kurono, N ;

Sugita, K ;

Takasugi, S ;

Tokuda, M .

TETRAHEDRON, 1999, 55 (19) :6097-6108

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