Synthesis of benzothieno[2,3-b]thiophenes, [2,3-b:3′,2′-d]-dithienothiophenes and their selenium derivatives via electrophilic cyclization and McMurry cyclization

被引：14

作者：

Geng, Weizhi ^{[1
,2
]}

Wang, Hanliu ^{[1
,2
]}

Wang, Zitao ^{[1
,2
]}

Zhang, Shaoguang ^{[1
,2
]}

Zhang, Wen-Xiong ^{[1
,2
]}

Xi, Zhenfeng ^{[1
,2
,3
]}

机构：

[1] Peking Univ, Coll Chem, BNLMS, Beijing 100871, Peoples R China

[2] Peking Univ, Coll Chem, Minist Educ, Key Lab Bioorgan Chem & Mol Engn, Beijing 100871, Peoples R China

[3] Chinese Acad Sci, SIOC, State Key Lab Organomet Chem, Shanghai 200032, Peoples R China

来源：

TETRAHEDRON | 2012年 / 68卷 / 26期

关键词：

Benzothieno[2,3-b]thiophene; Dilithio reagent; Dithienothiophene; Electrophilic cyclization; McMurry cyclization; FIELD-EFFECT TRANSISTORS; LOW-VALENT TITANIUM; CROSS-CONJUGATED OLIGOTHIOPHENES; ONE-STEP SYNTHESIS; HIGH-PERFORMANCE; ASYMMETRIC-SYNTHESIS; CARBON-SULFUR; ORGANIC SEMICONDUCTOR; CATALYZED CYCLIZATION; COUPLING REACTIONS;

D O I：

10.1016/j.tet.2012.01.088

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Benzothieno[2,3-b]thiophenes, [2,3-b:3',2'-d]-dithienothiophenes, and their selenium derivatives were synthesized in good yields from readily available 3-ethynyllithio-benzo[b]thiophenyllithio compounds, sulfur or selenium, and 2 equiv of acid chlorides. Two heteroarene rings were constructed by a twofold cyclization via an acid chloride-induced electrophilic ring closing and the McMurry cyclization using Zn/TiCl4 reagents. (C) 2012 Elsevier Ltd. All rights reserved.

引用

页码：5283 / 5289

页数：7

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