1263771-51-2Relevant academic research and scientific papers
Syntheses of substituted benzosiloles and siloles by diisobutylaluminium hydride-promoted cyclization of 1-silyl-2-(2-silylethynyl)benzenes and 1,4-disilylalk-3-en-1-ynes
Kinoshita, Hidenori,Fukumoto, Hiroki,Ueda, Akihiro,Miura, Katsukiyo
, p. 1632 - 1645 (2018/02/19)
An efficient method for preparing substituted benzosiloles and unsymmetrically substituted siloles by intramolecular C-Si bond formation has been developed. The reaction of 1-methoxysilyl-2-[2-(trimethylsilyl)ethynyl]benzenes with 1.5 equiv of diisobutylaluminium hydride (DIBAL-H) gave benzosiloles in good to high yields. Similarly 4-methoxysilyl-1-silylalk-3-en-1-ynes were cyclized to multisubstituted siloles. Mechanistic study of this transformation uncovered that the methoxysilyl group was initially converted into the corresponding hydrosilyl group by the action of DIBAL-H, and that the resultant hydrosilanes underwent the DIBAL-H-promoted cyclization to benzosiloles. When 1-hydrosilyl-2-[2-(trimethylsilyl)ethynyl]benzenes were used as substrates, a substoichiometric amount of DIBAL-H was enough for the cyclization. The DIBAL-H-promoted transformation could be applied to regio-defined synthesis of unsymmetrically substituted siloles from 4-hydrosilyl-1-silylalk-3-en-1-ynes. This pre-installation approach provides a straightforward access to multisubstituted siloles with complete regioselection.
Hydrosilylation-metathesis sequence leading to 1-silaindenes
Matsuda, Takanori,Yamaguchi, Yoshiyuki,Ishida, Naoki,Murakami, Masahiro
supporting information; experimental part, p. 2743 - 2746 (2010/12/29)
1-Silaindenes are prepared starting from (2-vinylphenyl)hydrosilanes and alkynes through a ruthenium-catalyzed hydrosilylation-ring-closing-metathesis sequence. The method is successfully applied to the synthesis of molecules containing multiple silaindene units.
