Palladium-catalyzed coupling reactions towards the synthesis of well-defined thiophene-oligomers

被引：27

作者：

Hassan, J

Gozzi, C

Schulz, E

Lemaire, M

机构：

[1] UCBL, UMR 5622, Lab Catalyse & Synthese Organ, CPE, F-69622 Villeurbanne, France

[2] Univ Paris 11, Lab Catalyse Mol, UMR 8075, ICMMO, F-91405 Orsay, France

来源：

JOURNAL OF ORGANOMETALLIC CHEMISTRY | 2003年 / 687卷 / 02期

关键词：

Heck-type and Ullmann-type reactions; regioregular oligothiophenes; thiophene; palladium acetate;

D O I：

10.1016/S0022-328X(03)00626-0

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Heck- and Ullmann-type palladium-catalyzed reactions were used in order to perform the synthesis of 3',4"-dioctyl-2,2',5'2",5",2"'-tetrathienyl. The desired oligothiophene was synthesized in five steps with a total yield of 38% by a Heck-type reaction of bromo-derivatives and a yield of 45% by an Ullmann-type reaction of iodo-precursors. (C) 2003 Elsevier B.V. All rights reserved.

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收藏

页码：280 / 283

页数：4

相关论文

共 18 条

[1] Synthesis and UV-visible properties of soluble regioregular oligo(3-octylthiophenes), monomer to hexamer [J].

Bidan, G ;

De Nicola, A ;

Enee, V ;

Guillerez, S .

CHEMISTRY OF MATERIALS, 1998, 10 (04) :1052-1058

[2] Synthesis, characterization and applications of thiophene-based functional polymers [J].

Chan, HSO ;

Ng, SC .

PROGRESS IN POLYMER SCIENCE, 1998, 23 (07) :1167-1231

[3] REGIOCONTROLLED SYNTHESIS OF POLY(3-ALKYLTHIOPHENES) MEDIATED BY RIEKE ZINC - THEIR CHARACTERIZATION AND SOLID-STATE PROPERTIES [J].

CHEN, TA ;

WU, XM ;

RIEKE, RD .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (01) :233-244

[4] Direct thiophene arylation catalysed by Palladium [J].

Gozzi, C ;

Lavenot, L ;

Ilg, K ;

Penalva, V ;

Lemaire, M .

TETRAHEDRON LETTERS, 1997, 38 (51) :8867-8870

[5] New convenient synthesis of highly regioregular poly(3-octylthiophene) based on the Suzuki coupling reaction [J].

Guillerez, S ;

Bidan, G .

SYNTHETIC METALS, 1998, 93 (02) :123-126

[6] Aryl-aryl bond formation one century after the discovery of the Ullmann reaction [J].

Hassan, J ;

Sévignon, M ;

Gozzi, C ;

Schulz, E ;

Lemaire, M .

CHEMICAL REVIEWS, 2002, 102 (05) :1359-1469

[7] Preparation of unsymmetrical biaryls via palladium-catalyzed coupling reaction of aryl halides [J].

Hassan, J ;

Hathroubi, C ;

Gozzi, C ;

Lemaire, M .

TETRAHEDRON, 2001, 57 (37) :7845-7855

[8] Catalytic alternative of the Ullmann reaction [J].

Hassan, J ;

Penalva, V ;

Lavenot, L ;

Gozzi, C ;

Lemaire, M .

TETRAHEDRON, 1998, 54 (45) :13793-13804

[9] Synthesis and characterisation of telechelic regioregular head-to-tail poly(3-alkylthiophenes) [J].

Iraqi, A ;

Barker, GW .

JOURNAL OF MATERIALS CHEMISTRY, 1998, 8 (01) :25-29

[10] Homologous series of regioregular alkylsubstituted oligothiophenes up to an 11-mer [J].

Krömer, J ;

Bäuerle, P .

TETRAHEDRON, 2001, 57 (17) :3785-3794