期刊
MOLECULES
卷 21, 期 8, 页码 -出版社
MDPI AG
DOI: 10.3390/molecules21080999
关键词
benzosilole; silyl cation; hydrosilylation; metal free
资金
- Ministry of Education, Culture, Sports, Science and Technology, Japan [26410035]
- Grants-in-Aid for Scientific Research [26410035] Funding Source: KAKEN
Diorganyl[2-(trimethylsilylethynyl)phenyl]silanes 1a-c andmethyl-substituted phenylsilanes 1d and 1e were treated with a small amount of trityl tetrakis(pentafluorophenyl) borate (TPFPB) as an initiator in benzene to afford the corresponding benzosiloles (2a-e) in moderate to good yields. However, no reaction was observed for the reaction using [2-(1-hexynyl)phenyl]diisopropylsilane lf. The methyl substituent was tolerated under the reaction conditions and increased the yield of the corresponding benzosilole depending on the substitution position. From the result using 1f, the current reaction was found to require the trimethylsilyl group, which can stabilize intermediary alkenyl carbocations by the beta-silyl effect. The current reaction can be considered an intramolecular chain hydrosilylation of alkynylarylsilanes involving silyl cations as chain carriers. Therefore, the silyl cations generated by hydride abstraction from hydrosilanes 1 with the trityl cation causes intramolecular electrophilic addition to the C-C triple bond to form ethenyl cations, which abstract a hydride from 1 to afford benzosiloles 2 with the regeneration of the silyl cations.
作者
我是这篇论文的作者
点击您的名字以认领此论文并将其添加到您的个人资料中。
推荐
暂无数据