Regioselective palladium-catalyzed cross-coupling reactions in the synthesis of novel 2,3-disubstituted thiophene derivatives

被引:54
作者
Pereira, R [1 ]
Iglesias, B [1 ]
de Lera, AR [1 ]
机构
[1] Univ Vigo, Fac Ciencias, Dept Quim Organ, Vigo 36200, Spain
关键词
thiophenes; Sonogashira reactions; Stille reactions; Suzuki reactions; heterocycles;
D O I
10.1016/S0040-4020(01)00764-5
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A reactivity optimization study of the palladium-catalyzed cross-coupling reactions of 2,3-dibromothiophene and organometallic reagents has been conducted. Regioselective coupling at the C2 position, accomplished most notably by Suzuki coupling, was combined with a Stille reaction at C3 using Fu's modification, to afford the 2,3-disubstituted thiophene derivatives. (C) 2001 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:7871 / 7881
页数:11
相关论文
共 56 条
[1]   Preparation of new polyfunctional magnesiated heterocycles using a chlorine-, bromine-, or iodine-magnesium exchange [J].
Abarbri, M ;
Thibonnet, J ;
Bérillon, L ;
Dehmel, F ;
Rottländer, M ;
Knochel, P .
JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (15) :4618-4634
[2]   ALKYNE ISOMERIZATION REAGENTS - MIXED ALKALI-METAL AMIDES [J].
ABRAMS, SR .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1984, 62 (07) :1333-1334
[3]  
Bach T, 1999, EUR J ORG CHEM, V1999, P2045
[4]   Radical hydrostannylation, Pd(0)-catalyzed hydrostannylation, stannylcupration of propargyl alcohols and enynols: Regio- and stereoselectivities [J].
Betzer, JF ;
Delaloge, F ;
Muller, B ;
Pancrazi, A ;
Prunet, J .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (22) :7768-7780
[5]   Self-assembly of regioregular, amphiphilic polythiophenes into highly ordered π-stacked conjugated polymer thin films and nanocircuits [J].
Bjornholm, T ;
Greve, DR ;
Reitzel, N ;
Hassenkam, T ;
Kjaer, K ;
Howes, PB ;
Larsen, NB ;
Bogelund, J ;
Jayaraman, M ;
Ewbank, PC ;
McCullough, RD .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (30) :7643-7644
[6]  
BRANDSMA B, 1998, APPL TRANSITION META, P26
[7]  
BRANDSMA B, 1998, APPL TRANSITION META, P222
[8]  
Brandsma L., 1998, SPRINGER LAB, P15
[9]   Preparation of 5-aryl furfurals and aryl thiophene-2-carboxaldehydes via palladium-catalyzed C-C bond formation in aqueous media [J].
Bussolari, JC ;
Rehborn, DC .
ORGANIC LETTERS, 1999, 1 (07) :965-967
[10]   NATURALLY-OCCURRING ACETYLENIC-COMPOUNDS AND DERIVATIVES - REGIOCONTROLLED AND STEREOCONTROLLED CHLOROFORMYLATION OF 2-(1-PROPYNYL)THIOPHENE AND 2-PHENYL-5-(1-PROPYNYL)THIOPHENE [J].
CARPITA, A ;
LEZZI, A ;
ROSSI, R ;
MARCHETTI, F ;
MERLINO, S .
TETRAHEDRON, 1985, 41 (03) :621-625