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

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