Improved synthesis of N-alkyl substituted dithieno[3,2-b:2′,3′-d]pyrroles

被引:61
作者
Koeckelberghs, G
De Cremer, L
Vanormelingen, W
Dehaen, W
Verbiest, T
Persoons, A
Samyn, C
机构
[1] Katholieke Univ Leuven, Lab Macromol & Phys Organ Chem, B-3001 Heverlee, Belgium
[2] Katholieke Univ Leuven, Lab Chem & Biol Dynam, B-3001 Heverlee, Belgium
[3] Katholieke Univ Leuven, Synth Organ Lab, B-3001 Heverlee, Belgium
关键词
D O I
10.1016/j.tet.2004.10.106
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A new, convergent and improved synthetic method to prepare N-alkyl substituted dithienopyrroles is described. The procedure consists of a Pd-catalyzed amination of 3,3'-dibromo-2,2'-bithiophene. The reaction conditions were optimized, which makes this method applicable to prepare these molecules easily in high yields and on a large scale. (C) 2004 Elsevier Ltd. All rights reserved.
引用
收藏
页码:687 / 691
页数:5
相关论文
共 14 条
[1]  
BERLIN A, 1992, MAKROMOL CHEM, V193, P399
[2]   Chirality in regioregular and soluble polythiophene: An internal probe of conformational changes induced by minute solvation variation [J].
Bidan, G ;
Guillerez, S ;
Sorokin, V .
ADVANCED MATERIALS, 1996, 8 (02) :157-&
[3]   A second-generation catalyst for aryl halide amination: Mixed secondary amines from aryl halides and primary amines catalyzed by (DPPF)PdCl2 [J].
Driver, MS ;
Hartwig, JF .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (30) :7217-7218
[4]   A soluble equivalent of the supramolecular, quasi-one-dimensional, semiconducting Magnus' green salt [J].
Fontana, M ;
Chanzy, H ;
Caseri, WR ;
Smith, P ;
Schenning, APHJ ;
Meijer, EW ;
Gröhn, F .
CHEMISTRY OF MATERIALS, 2002, 14 (04) :1730-1735
[5]  
Hartwig JF, 1998, ANGEW CHEM INT EDIT, V37, P2046, DOI 10.1002/(SICI)1521-3773(19980817)37:15<2046::AID-ANIE2046>3.0.CO
[6]  
2-L
[7]   SELECTIVE FUNCTIONALIZATION OF 2,2'-BITHIOPHENES [J].
KHOR, E ;
SIU, CN ;
HWEE, CL ;
CHAI, S .
HETEROCYCLES, 1991, 32 (09) :1805-1812
[8]   THE USE OF DIETHYL AZODICARBOXYLATE AND TRIPHENYLPHOSPHINE IN SYNTHESIS AND TRANSFORMATION OF NATURAL-PRODUCTS [J].
MITSUNOBU, O .
SYNTHESIS-STUTTGART, 1981, (01) :1-28
[9]   The double N-arylation of primary amines:: Toward multisubstituted carbazoles with unique optical properties [J].
Nozaki, K ;
Takahashi, K ;
Nakano, K ;
Hiyama, T ;
Tang, HZ ;
Fujiki, M ;
Yamaguchi, S ;
Tamao, K .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (18) :2051-2053
[10]   A simple and efficient route to N-functionalized dithieno[3,2-b:2′,3′-d]pyrroles:: Fused-ring building blocks for new conjugated polymeric systems [J].
Ogawa, K ;
Rasmussen, SC .
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (07) :2921-2928