Synthesis of 4,7′-Bibenzo[ b ]thiophenes Bearing Several Different Substituents at 2-, 2′-, 4′-, and 7-Positions; Structurally Featured Molecular Scaffolds for Selective Substitution

被引：0
|
作者：
Mikami, Shinichi [1 ]
Matsuo, Akihiro [1 ]
Kwon, Eunsang [2 ]
Toyota, Kozo [1 ]
机构：
[1] Tohoku Univ, Grad Sch Sci, Dept Chem, Aoba Ku, Sendai, Miyagi 9808578, Japan
[2] Tohoku Univ, Res & Analyt Ctr Giant Mol, Grad Sch Sci, Aoba Ku, Sendai, Miyagi 9808578, Japan
来源：
SYNLETT | 2021年 / 32卷 / 18期
基金：
日本学术振兴会;
关键词：
bibenzothiophene building block; multihalomolecular scaffold; molecular architecture; orthogonal structure; CATALYZED DIRECT ARYLATION;
D O I：
10.1055/s-0040-1719839
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Four isomers of 4,7 '-bibenzothiophene scaffolds bearing two different halogen (Br, Cl) and triisopropylsilyl substituents have been synthesized from the two multihalobenzo[ b ]thiophenes via iodoselective Miyaura borylation reaction using potassium benzoate as a base. Further investigation into the reactivity of 4,7 '-bibenzothiophenes in substitution reaction, Suzuki-Miyaura cross-coupling reaction, and C-H direct arylation reaction revealed that tetrasubstituted 4,7 '-bibenzothiophenes can be synthesized site- (chemo-) selectively, which are promising novel components for molecular architecture.
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页码：1826 / 1832
页数：7
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