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 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 cm2/Vs in an amorphous film, making this class of compounds promising electronic materials for organic light emitting devices and organic photovoltaic cells.
Ilies
Laurean
L
Department of Chemistry, School of Science, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-0033, Japan.
Tsuji
Hayato
H
Sato
Yoshiharu
Y
Nakamura
Eiichi
E
D000473:Alkanes / Q000737:chemistry*; D001952:Bridged-Ring Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D015394:Molecular Structure; D017646:Organosilicon Compounds / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism; D014001:Tin / Q000737:chemistry*
D000473:Alkanes; D001952:Bridged-Ring Compounds; D017646:Organosilicon Compounds; D014001:Tin