Direct C-H arylation of 3-methoxythiophene catalyzed by Pd.: Application to a more efficient synthesis of π-alkoxy-oligothiophene derivatives

被引：57

作者：

Borghese, A. ^{[1
]}

Geldhof, G. ^{[1
]}

Antoine, L. ^{[1
]}

机构：

[1] Lilly Dev Ctr SA, Chem Prod Res & Dev, B-1348 Mont St Guibert, Belgium

来源：

TETRAHEDRON LETTERS | 2006年 / 47卷 / 52期

关键词：

D O I：

10.1016/j.tetlet.2006.10.130

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The direct regioselective C-H arylation of 3-methoxythiophene and 3,4-ethylenedioxythiophene (EDOT) was performed successfully under 'Heck-type' experimental conditions. This novel synthetic methodology has been used to prepare in a more simple way a series of oligothiophenes interesting for the electronic industry to build new synthetic organic materials. (c) 2006 Elsevier Ltd. All rights reserved.

引用

页码：9249 / 9252

页数：4

共 14 条

[1] Apperloo JJ, 2002, CHEM-EUR J, V8, P2384, DOI 10.1002/1521-3765(20020517)8:10<2384::AID-CHEM2384>3.0.CO
[2] 2-L
[3] Regioselective palladium-catalyzed arylation of 3-carboalkoxy furan and thiophene
Glover, B
Harvey, KA
Liu, B
Sharp, MJ
Tymoschenko, MF
[J]. ORGANIC LETTERS, 2003, 5 (03) : 301 - 304
[4] C-H bond functionalization in complex organic synthesis
Godula, K
Sames, D
[J]. SCIENCE, 2006, 312 (5770) : 67 - 72
[5] Direct thiophene arylation catalysed by Palladium
Gozzi, C
Lavenot, L
Ilg, K
Penalva, V
Lemaire, M
[J]. TETRAHEDRON LETTERS, 1997, 38 (51) : 8867 - 8870
[6] Aryl-aryl bond formation one century after the discovery of the Ullmann reaction
Hassan, J
Sévignon, M
Gozzi, C
Schulz, E
Lemaire, M
[J]. CHEMICAL REVIEWS, 2002, 102 (05) : 1359 - 1469
[7] On the efficiency of tetraalkylammonium salts in Heck type reactions
Jeffery, T
[J]. TETRAHEDRON, 1996, 52 (30) : 10113 - 10130
[8] MATHIEU T, 2005, CHEM-EUR J, V11, P3742
[9] SYNTHESIS OF BETA-METHOXY, METHYL-CAPPED ALPHA-OLIGOTHIOPHENES
MILLER, LL
YU, Y
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (21) : 6813 - 6819
[10] Functionalization of 3,4-ethylenedioxythiophene
Mohanakrishnan, AK
Hucke, A
Lyon, MA
Lakshmikantham, MV
Cava, MP
[J]. TETRAHEDRON, 1999, 55 (40) : 11745 - 11754

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