Abstract
Diorganyl[2-(trimethylsilylethynyl)phenyl]silanes 1a–c and methyl-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 β-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.
Highlights
A benzosilole is an attractive compound due to its emission property and potential use as of optical materials [1,2,3,4]
Diorganyl[2-(trimethylsilylethynyl)phenyl]silanes were reacted a to small amount
Diorganyl[2-(trimethylsilylethynyl)phenyl]silanes 1a–c were reacted with a small amount
Summary
A benzosilole is an attractive compound due to its emission property and potential use as of optical materials [1,2,3,4]. The intramolecular addition athe silyl cation of toward a C–C triple bond rather using than an intermolecular one is expected to lead toof a the synthesis synthesis of 1,2-dihydro-2-silanaphthalenes using alkynes [25,26]. The addition a silyl cationbyof toward a C–C triple bondofrather than intermolecular oneintramolecular isHerein, expected lead to benzosilole an appropriate reaction the resulting ethenyl[25,26]. Wetoreport thea a silyl cation toward a C–C triple bond rather than anan intermolecular one is isexpected totolead totoa of a silyl cation toward a C–C triple bond rather than intermolecular one expected lead benzosilole by chain an appropriate reaction of the resulting ethenyl carbocation. We with report the intramolecular hydrosilylation of diorganyl[2-(trimethylsilylethynyl)phenyl]silanes trityl benzosilole by an appropriate reaction of the resulting ethenyl carbocation. Intramolecular chain chain hydrosilylation hydrosilylation of of diorganyl[2-(trimethylsilylethynyl)phenyl]silanes diorganyl[2-(trimethylsilylethynyl)phenyl]silanes with with trityl trityl intramolecular tetrakis(pentafluorophenyl)borate tetrakis(pentafluorophenyl)borate (TPFPB) as an initiator
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