Synthesis of thiophene derivatives via palladium-catalyzed coupling reactions

被引：45

作者：

Arai, Nobumichi ^{[1
]}

Miyaoku, Takayuki ^{[1
]}

Teruya, Shota ^{[1
]}

Mori, Atsunori ^{[1
]}

机构：

[1] Kobe Univ, Dept Sci & Chem Engn, Kobe, Hyogo 6578501, Japan

来源：

TETRAHEDRON LETTERS | 2008年 / 49卷 / 06期

关键词：

thiophene; corey-fuchs reaction; palladium catalyst; Suzuki-Miyaura coupling; CH arylation;

D O I：

10.1016/j.tetlet.2007.12.010

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Thiophene derivatives with multiple substitutions are prepared from vinylidene bromide, which is synthesized by the reaction of thiophene-2-carboxaldehyde with carbon tetrabromide in the presence of PPh(3), as a core molecule through several coupling reactions such as Suzuki-Miyaura coupling and palladium-catalyzed CH arylation. The reactions with a wide variety of organic halides lead to a series of substituted thiophene derivatives in moderate to good yields. (c) 2007 Elsevier Ltd. All rights reserved.

引用

页码：1000 / 1003

页数：4

共 37 条

[1] Palladium-catalyzed intramolecular CH arylation of five-membered N-heterocycles [J].

Arai, Nobumichi ;

Takahashi, Masabumi ;

Mitani, Makoto ;

Mori, Atsunori .

SYNLETT, 2006, (18) :3170-3172

[2]

Briehn CA, 2001, ANGEW CHEM INT EDIT, V40, P4680, DOI 10.1002/1521-3773(20011217)40:24<4680::AID-ANIE4680>3.0.CO

[3]

2-X

[4]

COREY EJ, 1972, TETRAHEDRON LETT, P3769

[5]

Corriu R.J. P., 1972, J CHEM SOC CHEM COMM, P144

[6] Building blocks for n-type organic electronics: Regiochemically modulated inversion of majority carrier sign in perfluoroarene-modified polythiophene semiconductors [J].

Facchetti, A ;

Yoon, MH ;

Stern, CL ;

Katz, HE ;

Marks, TJ .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (33) :3900-3903

[7] High ambipolar mobility in a highly ordered smectic phase of a dialkylphenylterthiophene derivative that can be applied to solution-processed organic field-effect transistors [J].

Funahashi, Masahiro ;

Zhang, Fapei ;

Tamaoki, Nobuyuki .

ADVANCED MATERIALS, 2007, 19 (03) :353-+

[8]

GOKULA K, 2006, SCIENCE, V312, P67

[9] Palladium-catalyzed coupling reactions towards the synthesis of well-defined thiophene-oligomers [J].

Hassan, J ;

Gozzi, C ;

Schulz, E ;

Lemaire, M .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2003, 687 (02) :280-283

[10] Synthesis and spectroscopic properties of a series of β-blocked long oligothiophenes up to the 96-mer:: Revaluation of effective conjugation length [J].

Izumi, T ;

Kobashi, S ;

Takimiya, K ;

Aso, Y ;

Otsubo, T .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (18) :5286-5287

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