Modular Synthesis of Functionalized Benzosiloles by Tin-Mediated Cyclization of (o-Alkynylphenyl)silane

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 synthes...

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Veröffentlicht in:Journal of the American Chemical Society 2008-04, Vol.130 (13), p.4240-4241
Hauptverfasser: Ilies, Laurean, Tsuji, Hayato, Sato, Yoshiharu, Nakamura, Eiichi
Format: Artikel
Sprache:eng
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Zusammenfassung: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 × 10-4 cm2/Vs in an amorphous film, making this class of compounds promising electronic materials for organic light emitting devices and organic photovoltaic cells.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja800636g