Synthesis of Novel 4,4-Dialkyl- and 4,4-Diarylindeno[1,2-b]Thiophenes and their 2-Bromo Derivatives

被引：5

作者：

Bucevicius, J. ^{[1
]}

Adomenas, P. ^{[2
]}

Tumkevicius, S. ^{[1
]}

机构：

[1] Vilnius Univ, LT-03225 Vilnius, Lithuania

[2] Fine Synth Ltd, LT-08311 Vilnius, Lithuania

来源：

CHEMISTRY OF HETEROCYCLIC COMPOUNDS | 2015年 / 50卷 / 10期

关键词：

indeno[1,2-b]thiophenes; sulfur heterocycles; alkylation; bromination; Kumada coupling; SENSITIZED SOLAR-CELLS; ORGANIC SEMICONDUCTORS; DYE; PERFORMANCE;

D O I：

10.1007/s10593-014-1605-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A series of new 4,4-dialkyl- and 4,4-diaryl-4H-indeno[1,2-b]thiophenes and their 2-bromo derivatives were synthesized and characterized. An economical one-pot method for the preparation of the key starting material 2-(2-thienyl)benzoic acid and improved procedures for the synthesis of indeno[1,2-b]thiophen-4-one and 4,4-dialkyl-4H-indeno[1,2-b]thiophenes have been developed. The described methods were shown to be efficient for the preparation of the title compounds on a multigram scale.

引用

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页码：1413 / 1420

页数：8

相关论文

共 17 条

[1] Manganese-Catalyzed Oxidative Cross-Coupling of Grignard Reagents with Oxygen as an Oxidant [J].

Cahiez, Gerard ;

Duplais, Christophe ;

Buendia, Julien .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (36) :6731-6734

[2] 4,9-Dihydro-4,4,9,9-tetrahexyl-s-indaceno[1,2-b:5,6-b′]dithiophene as a π-Spacer of Donor-π-Acceptor Dye and Its Photovoltaic Performance with Liquid and Solid-State Dye-Sensitized Solar Cells [J].

Cai, Liping ;

Moehl, Thomas ;

Moon, Soo-Jin ;

Decoppet, Jean-David ;

Humphry-Baker, Robin ;

Xue, Zhaosheng ;

Bin, Liu ;

Zakeeruddin, Shaik M. ;

Graetzel, Michael .

ORGANIC LETTERS, 2014, 16 (01) :106-109

[3] Structural effects on the hole mobilities of indenothiophene-embedded homologs [J].

Chao, Teng-Chih ;

Wong, Ken-Tsung ;

Hung, Wen-Yi ;

Hou, Tei-Hung ;

Chen, Wei-Jiun .

TETRAHEDRON LETTERS, 2009, 50 (26) :3422-3424

[4] Molecular engineering of organic sensitizers for highly efficient gel-state dye-sensitized solar cells [J].

Choi, Hyeju ;

Paek, Sanghyun ;

Lim, Kimin ;

Kim, Chulwoo ;

Kang, Moon-Sung ;

Song, Kihyung ;

Ko, Jaejung .

JOURNAL OF MATERIALS CHEMISTRY A, 2013, 1 (28) :8226-8233

[5] Synthesis of 4-aryl-, 2,4-diaryl- and 2,4,7-triarylpyrrolo[2,3-d]pyrimidines by a combination of the Suzuki cross-coupling and N-arylation reactions [J].

Dodonova, Jelena ;

Skardziute, Lina ;

Kazlauskas, Karolis ;

Jursenas, Saulius ;

Tumkevicius, Sigitas .

TETRAHEDRON, 2012, 68 (01) :329-339

[6] New Efficient Ruthenium Sensitizers with Unsymmetrical Indeno[1,2-b]thiophene or a Fused Dithiophene Ligand for Dye-Sensitized Solar Cells [J].

Kim, Jeum-Jong ;

Lim, Kimin ;

Choi, Hyunbong ;

Fan, Shengqiang ;

Kang, Moon-Sung ;

Gao, Guohua ;

Kang, Hong Seok ;

Ko, Jaejung .

INORGANIC CHEMISTRY, 2010, 49 (18) :8351-8357

[7] CHEMISTRY OF INDENOTHIOPHENES .2. 4H-INDENO 1,2-B!THIOPHENE AND 8H-INDENO 1,2-C!THIOPHENE [J].

MACDOWEL.DW ;

JEFFRIES, AT .

JOURNAL OF ORGANIC CHEMISTRY, 1970, 35 (04) :871-&

[8] Palladium-catalyzed Stille cross-coupling reaction of aryl chlorides using a pre-milled palladium acetate and XPhos catalyst system [J].

Naber, John R. ;

Buchwald, Stephen L. .

ADVANCED SYNTHESIS & CATALYSIS, 2008, 350 (7-8) :957-961

[9] Quaterthiophenes with Terminal Indeno[1,2-b]thiophene Units as p-Type Organic Semiconductors [J].

Pouchain, Laurent ;

Aleveque, Olivier ;

Nicolas, Yohann ;

Oger, Agathe ;

Le Regent, Charles-Henri ;

Allain, Magali ;

Blanchard, Philippe ;

Roncali, Jean .

JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (03) :1054-1064

[10] Palladium-Catalyzed Intermolecular Desulfinylative Cross-Coupling of Heteroaromatic Sulfinates [J].

Sevigny, Stephane ;

Forgione, Pat .

CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (07) :2256-2260