Synthesis of 5-Alkyl[3,4-c]thienopyrrole-4,6-dione-Based Polymers by Direct Heteroarylation

被引：216

作者：

Berrouard, Philippe ^{[1
]}

Najari, Ahmed ^{[1
]}

Pron, Agnieszka ^{[1
]}

Gendron, David ^{[1
]}

Morin, Pierre-Olivier ^{[1
]}

Pouliot, Jean-Remi ^{[1
]}

Veilleux, Justine ^{[1
]}

Leclerc, Mario ^{[1
]}

机构：

[1] Univ Laval, Dept Chem, Quebec City, PQ G1V 0A6, Canada

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2012年 / 51卷 / 09期

基金：

加拿大自然科学与工程研究理事会;

关键词：

heteroarylation; homogeneous catalysis; palladium; polymerization; thieno[3; 4-c]pyrrole-4; 6-dione; CATALYZED DIRECT ARYLATION; HETEROJUNCTION SOLAR-CELLS; HETEROAROMATIC-COMPOUNDS; CRYSTALLINITY; DONOR;

D O I：

10.1002/anie.201106411

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Don't stand Stille: A direct heteroarylation polycondensation reaction was used for the synthesis of high-molecular-weight thienopyrroledione-based polymers (see scheme) in an impressive yield (up to 96 %) and in only a few synthetic steps. This new method is an alternative to the standard Stille coupling reaction and thus avoids formation of toxic tin by-products. Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：2068 / 2071

页数：4

共 36 条

[1]

Ackermann L., 2009, ANGEW CHEM, V121, P9976, DOI DOI 10.1002/ANGE.200902996

[2] Carboxylate-Assisted Transition-Metal-Catalyzed C-H Bond Functionalizations: Mechanism and Scope [J].

Ackermann, Lutz .

CHEMICAL REVIEWS, 2011, 111 (03) :1315-1345

[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] Dithienogermole As a Fused Electron Donor in Bulk Heterojunction Solar Cells [J].

Amb, Chad M. ;

Chen, Song ;

Graham, Kenneth R. ;

Subbiah, Jegadesan ;

Small, Cephas E. ;

So, Franky ;

Reynolds, John R. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (26) :10062-10065

[5]

[Anonymous], 2009, ANGEW CHEM INT ED

[6]

[Anonymous], 1999, ANGEW CHEM INT ED

[7] Palladium-Catalyzed Direct Arylation of Heteroaromatic Compounds: Improved Conditions Utilizing Controlled Microwave Heating [J].

Baghbanzadeh, Mostafa ;

Pilger, Christian ;

Kappe, C. Oliver .

JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (19) :8138-8142

[8] Stille Polycondensation for Synthesis of Functional Materials [J].

Carsten, Bridget ;

He, Feng ;

Son, Hae Jung ;

Xu, Tao ;

Yu, Luping .

CHEMICAL REVIEWS, 2011, 111 (03) :1493-1528

[9] Crystalline conjugated polymer containing fused 2,5-di(thiophen-2-yl)thieno[2,3-b]thiophene and thieno[3,4-c]pyrrole-4,6-dione units for bulk heterojunction solar cells [J].

Chen, Guan-Yu ;

Cheng, Yu-Hsin ;

Chou, Yi-Jen ;

Su, Ming-Shin ;

Chen, Chia-Min ;

Wei, Kung-Hwa .

CHEMICAL COMMUNICATIONS, 2011, 47 (17) :5064-5066

[10] Palladium-catalysed direct arylation of thiophenes tolerant to silyl groups [J].

Chen, Lu ;

Roger, Julien ;

Bruneau, Christian ;

Dixneuf, Pierre H. ;

Doucet, Henri .

CHEMICAL COMMUNICATIONS, 2011, 47 (06) :1872-1874

← 1 2 3 4 →