Copper(I)-catalysed homo-coupling of aryldiazonium salts: synthesis of symmetrical biaryls

被引：45

作者：

Cepanec, Ivica ^{[1
]}

Litvic, Mladen ^{[1
]}

Udikovic, Josipa ^{[1
]}

Pogorelic, Ivan ^{[1
]}

Lovric, Marija ^{[1
]}

机构：

[1] BELUPO Pharmaceut & Cosmet Inc, Res Dept, Zagreb 10000, Croatia

来源：

TETRAHEDRON | 2007年 / 63卷 / 25期

关键词：

aryldiazonium salts; symmetrical biaryls; homo-coupling; copper(I) triflate; 2,2'-bipyridine;

D O I：

10.1016/j.tet.2007.04.016

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Copper(I) triflate acts as an efficient stoichiometric reagent for the homo-coupling of aryldiazonium salts bearing electron-withdrawing group(s), to yield symmetrical biaryls in acetonitrile under mild reaction conditions. Aryldiazonium salts bearing electron-donating groups undergo the reaction by using catalytic amounts of a copper complex prepared in situ from copper(II) triflate and 2,2'-bipyridine with metallic copper as an ultimate reductant. (C) 2007 Elsevier Ltd. All rights reserved.

引用

页码：5614 / 5621

页数：8

共 59 条

[1] Oxidative addition of aryl halides to transient anionic sigma-aryl-palladium(0) intermediates - Application to palladium-catalyzed reductive coupling of aryl halides [J].

Amatore, C ;

Carre, E ;

Jutand, A ;

Tanaka, H ;

Ren, QH ;

Torii, S .

CHEMISTRY-A EUROPEAN JOURNAL, 1996, 2 (08) :957-966

[2] Palladium-imidazolium carbene catalyzed aryl, vinyl, and alkyl Suzuki-Miyaura cross coupling [J].

Andrus, MB ;

Song, C .

ORGANIC LETTERS, 2001, 3 (23) :3761-3764

[3]

Atkinson E. R., 1941, ORG SYNTH, V1, P222

[4]

BAMFIELD P, 1978, SYNTHESIS-STUTTGART, P537

[5] PHASE-TRANSFER-CATALYZED GOMBERG-BACHMANN SYNTHESIS OF UNSYMMETRICAL BIARENES - A SURVEY OF CATALYSTS AND SUBSTRATES [J].

BEADLE, JR ;

KORZENIOWSKI, SH ;

ROSENBERG, DE ;

GARCIASLANGA, BJ ;

GOKEL, GW .

JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (09) :1594-1603

[6]

BJORKLUND C, 1966, TETRAHEDRON LETT, P675

[7]

Bonfand E, 2000, SYNLETT, P475

[8] THE DIRECTED SYNTHESIS OF BIARYL COMPOUNDS - MODERN CONCEPTS AND STRATEGIES [J].

BRINGMANN, G ;

WALTER, R ;

WEIRICH, R .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1990, 29 (09) :977-991

[9] New highly active chiral phosphapalladacycle catalysts. First isolation and characterization of a Pd(IV) intermediate [J].

Brunel, JM ;

Hirlemann, MH ;

Heumann, A ;

Buono, G .

CHEMICAL COMMUNICATIONS, 2000, (19) :1869-1870

[10]

CARTER SD, 1985, J CHEM RES-S, P136

← 1 2 3 4 5 6 →