Modular synthesis of functionalized benzosiloles by tin-mediated cyclization of (o-alkynylphenyl)silane

被引:61
作者
Ilies, Laurean [1 ]
Tsuji, Hayato [1 ]
Sato, Yoshiharu [2 ]
Nakamura, Eiichi [1 ,2 ]
机构
[1] Univ Tokyo, Sch Sci, Dept Chem, Bunkyo Ku, Tokyo 1130033, Japan
[2] Univ Tokyo, Sch Sci, Dept Chem,Bunkyo Ku, Japan Sci & Technol Agcy,ERATO,Nakamura Funct Car, Tokyo 1130033, Japan
关键词
D O I
10.1021/ja800636g
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Trimethylstannyllithium promotes cyclization of (o-alkynylphenyl) silane into a 3-stannylbenzosilole, via addition to the triple bond followed by intramolecular cyclization in a cascade fashion. This intermediate can be functionalized with either electrophiles or nucleophiles to allow modular synthesis of 2,3-disubstituted benzosiloles. One of these compounds, a phenylene-bis (benzosilole) compound, shows electron drift mobility as high as 6 x 10(-4) cm(2/)Vs in an amorphous film, making this class of compounds promising electronic materials for organic light emitting devices and organic photovoltaic cells.
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收藏
页码:4240 / +
页数:3
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