One-pot Synthesis of Benzo[b]thiophenes and Benzo[b]selenophenes from o-Halo-Substituted Ethynylbenzenes: Convenient Approach to Mono-, Bis-, and Tris-Chalcogenophene-Annulated Benzenes

被引：180

作者：

Kashiki, Tomoya ^{[1
]}

Shinamura, Shoji ^{[1
]}

Kohara, Masahiro ^{[1
]}

Miyazaki, Eigo ^{[1
]}

Takimiya, Kazuo ^{[1
,2
]}

Ikeda, Masaaki ^{[3
]}

Kuwabara, Hirokazu ^{[3
]}

机构：

[1] Hiroshima Univ, Dept Appl Chem, Grad Sch Engn, Higashihiroshima 7398527, Japan

[2] Hiroshima Univ, Inst Adv Mat Res, Higashihiroshima 7398530, Japan

[3] Nippon Kayaku Co Ltd, Funct Chem R&D Labs, Kita Ku, Tokyo 1158588, Japan

来源：

ORGANIC LETTERS | 2009年 / 11卷 / 11期

关键词：

FIELD-EFFECT TRANSISTORS; HIGH-PERFORMANCE SEMICONDUCTORS; STAR-SHAPED OLIGOTHIOPHENES; CHARGE-TRANSFER COMPLEXES; LIGHT-EMITTING DEVICES; ELECTROPHILIC CYCLIZATION; ORGANIC SEMICONDUCTORS; FACILE SYNTHESIS; DERIVATIVES; BENZODITHIOPHENE;

D O I：

10.1021/ol900809w

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A convenient one-pot procedure for the synthesis of benzo[b]thiophenes and selenophenes from readily available o-halo-ethynylbenzene precursors is described. Regardless of the substituent on the acetylene terminus or the number of cyclization moieties on the precursors, various benzo[b]thiophenes and selenophenes, including not only the parent, alkyl-, and phenyl-substituted derivatives but also benzo[1,2-b:4,5-b']dithiophenes and diselenophenes and benzo[1,2-b:3,4-b':5,6-b '']trithiophenes and triselenophenes can be prepared in good to high yields.

引用

页码：2473 / 2475

页数：3

共 35 条

[1]

[Anonymous], 1999, J SULFUR CHEM

[2] NUCLEOPHILIC AROMATIC-SUBSTITUTION REACTIONS OF UNACTIVATED ARYL HALIDES WITH THIOLATE IONS IN HEXAMETHYLPHOSPHORAMIDE [J].

COGOLLI, P ;

MAIOLO, F ;

TESTAFERRI, L ;

TINGOLI, M ;

TIECCO, M .

JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (15) :2642-2646

[3] Planarized star-shaped oligothiophenes as a new class of organic semiconductors for heterojunction solar cells [J].

de Bettignies, R ;

Nicolas, Y ;

Blanchard, P ;

Levillain, E ;

Nunzi, JM ;

Roncali, J .

ADVANCED MATERIALS, 2003, 15 (22) :1939-1943

[4] Highly soluble [1]benzothieno[3,2-b]benzothiophene (BTBT) derivatives for high-performance, solution-processed organic field-effect transistors [J].

Ebata, Hideaki ;

Izawa, Takafumi ;

Miyazaki, Eigo ;

Takimiya, Kazuo ;

Ikeda, Masaaki ;

Kuwabara, Hirokazu ;

Yui, Tatsuto .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (51) :15732-+

[5] Synthesis, properties, and structures of benzo[1,2-b:4,5-b′]bis[b]benzothiophene and benzo[1,2-b:4,5-b′]bis[b]benzoselenophene [J].

Ebata, Hideaki ;

Miyazaki, Eigo ;

Yamamoto, Tatsuya ;

Takimiya, Kazuo .

ORGANIC LETTERS, 2007, 9 (22) :4499-4502

[6]

Engel E. O., 1994, METHODEN ORGANISCH E, VE6b, P217

[7] High-performance field-effect transistor based on dibenzo[d,d′]thieno[3,2-b;4,5-b′]dithiophene, an easily synthesized semiconductor with high ionization potential [J].

Gao, Jianhua ;

Li, Rongjin ;

Li, Liqiang ;

Meng, Qing ;

Jiang, Hui ;

Li, Hongxiang ;

Hu, Wenping .

ADVANCED MATERIALS, 2007, 19 (19) :3008-+

[8] Dipolar dibenzothiophene SS-dioxide derivatives containing diarylamine: Materials for single-layer organic light-emitting devices [J].

Huang, TH ;

Lin, JT ;

Chen, LY ;

Lin, YT ;

Wu, CC .

ADVANCED MATERIALS, 2006, 18 (05) :602-+

[9] A simple synthesis of angular anthrathiophenediones via acetylenic derivatives of anthraquinone [J].

Ivanchikova, ID ;

Lebedeva, NI ;

Shvartsberg, MS .

SYNTHESIS-STUTTGART, 2004, (13) :2131-2134

[10] PHOTOCYCLIZATION OF TERTHIOPHENES [J].

JAYASURIYA, N ;

KAGAN, J ;

OWENS, JE ;

KORNAK, EP ;

PERRINE, DM .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (17) :4203-4205

← 1 2 3 4 →