Highly Efficient Activation of Organosilanes with 畏2-Aldehyde Nickel Complexes: Key for Catalytic Syntheses of Aryl-, Vinyl-, and Alkynyl-Benzoxasiloles

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• 作者：Yoichi Hoshimoto ; Hayato Yabuki ; Ravindra Kumar ; Haruka Suzuki ; Masato Ohashi ; Sensuke Ogoshi
• 刊名：Journal of the American Chemical Society
• 出版年：2014
• 出版时间：December 3, 2014
• 年：2014
• 卷：136
• 期：48
• 页码：16752-16755
• 全文大小：335K
• ISSN：1520-5126

文摘

An 畏²-aldehyde nickel complex was utilized as an effective activator for an organosilane in order to generate a hypervalent silicate reactant for the first time. This method was successfully applied to the highly efficient syntheses of 3-aryl-, vinyl-, and alkynyl-2,1-benzoxasiloles from benzaldehydes with aryl-, vinyl-, and alkynylsilyl groups at the ortho position. Initial mechanistic studies revealed that an intermolecular aryl transfer process was involved in the reaction mechanism. The formation of an 畏²-aldehyde complex was directly confirmed by NMR.