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Keywords = benzosilole

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24 pages, 15017 KiB  
Review
Advances in Synthesis of π-Extended Benzosilole Derivatives and Their Analogs
by Tuan Thanh Dang, Hue Minh Thi Nguyen, Hien Nguyen, Tran Ngoc Dung, Minh Tho Nguyen and Wim Dehaen
Molecules 2020, 25(3), 548; https://doi.org/10.3390/molecules25030548 - 27 Jan 2020
Cited by 18 | Viewed by 4962
Abstract
Benzosiloles and their π-extended derivatives are present in many important advanced materials due to their excellent physical properties. Especially, they have found many potential applications in the development of novel electronic materials such as OLEDs, semiconductors and solar cells. In this review, we [...] Read more.
Benzosiloles and their π-extended derivatives are present in many important advanced materials due to their excellent physical properties. Especially, they have found many potential applications in the development of novel electronic materials such as OLEDs, semiconductors and solar cells. In this review, we have summarized several main approaches to construct (di)benzosilole derivatives and (benzo)siloles fused to aromatic five- and six-membered heterocycles. Full article
(This article belongs to the Special Issue Development of New Methods of Synthesis of Heterocycles)
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7 pages, 921 KiB  
Article
Intramolecular Chain Hydrosilylation of Alkynylphenylsilanes Using a Silyl Cation as a Chain Carrier
by Hidekazu Arii, Kenichi Nakabayashi, Kunio Mochida and Takayuki Kawashima
Molecules 2016, 21(8), 999; https://doi.org/10.3390/molecules21080999 - 1 Aug 2016
Cited by 28 | Viewed by 5646
Abstract
Diorganyl[2-(trimethylsilylethynyl)phenyl]silanes 1ac 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 (2ae) in moderate to good yields. However, no reaction [...] Read more.
Diorganyl[2-(trimethylsilylethynyl)phenyl]silanes 1ac 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 (2ae) 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. Full article
(This article belongs to the Special Issue Advances in Silicon Chemistry)
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