94138-33-7Relevant 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.
Hybrid metal/organo relay catalysis enables enynes to be latent dienes for asymmetric diels-alder reaction
Han, Zhi-Yong,Chen, Dian-Feng,Wang, Ya-Yi,Guo, Rui,Wang, Pu-Sheng,Wang, Chao,Gong, Liu-Zhu
supporting information; experimental part, p. 6532 - 6535 (2012/06/15)
The hybrid Au(I)/Bronsted acid binary catalyst system enables enynes to serve as latent 1,3-silyloxydienes capable of participating in the first cascade hydrosiloxylation of an enynyl silanol/asymmetric Diels-Alder reaction. A variety of polycyclic compounds bearing multistereogenic centers were obtained in high yields and excellent enantioselectivities from the relay catalytic cascade reaction between (2-(but-3-en-1-ynyl)phenyl) silanols and quinones catalyzed by the combined achiral gold complex and chiral N-triflyl phosphoramide.
Synthesis of benzo[b]siloles via KH-promoted cyclization of (2-Alkynylphenyl)silanes
Llies, Laurean,Tsuji, Hayato,Nakamura, Eiichi
supporting information; experimental part, p. 3966 - 3968 (2009/12/03)
(Figure Presented) (2-Alkynylphenyl)silanes undergo intramolecular cyclization in the presence of an excess or a subequimolar amount of potassium hydride to give a variety of new 2-substituted benzosiloles in good to excellent yields. Some of these compou
