Synthesis of an NHC-Coordinated Dialkyldisilavinylidene and Its Oxidation Providing a Silicon Analog of an Acetolactone,Organometallics

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Synthesis of an NHC-Coordinated Dialkyldisilavinylidene and Its Oxidation Providing a Silicon Analog of an Acetolactone
Organometallics ( IF 2.5 ) Pub Date : 2021-04-01 , DOI: 10.1021/acs.organomet.1c00130
Ryo Kobayashi ₁ , Shintaro Ishida ₁ , Takeaki Iwamoto ₁

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Although isolable silicon analogs of acetylene have been extensively studied, the silicon analogs of vinylidene, which is a short-lived isomer of acetylene, remain scarce. Herein, we report isolable NHC-coordinated dialkyldisilavinylidene 1 synthesized by the reduction of a tetrabromodisilane featuring a bulky alkyl protecting group. 1 was fully characterized by a combination of multinuclear NMR spectroscopy, high-resolution mass spectrometry, elemental analysis, and X-ray diffraction analysis. The UV–vis spectrum and DFT calculations disclosed that 1 possesses an Si═Si double bond and lone pair electrons on the terminal Si atom coordinated by the NHC. 1 reacted with N₂O and B(C₆F₅)₃ to provide a silicon analog of an acetolactone stabilized by a Lewis base and a Lewis acid (4).

中文翻译：

NHC配位的二烷基二硅亚乙烯基叉的合成及其氧化，提供乙酰内酯的硅类似物

尽管已经对乙炔的可分离的硅类似物进行了广泛的研究，但作为乙炔的短寿命异构体的亚乙烯基的硅类似物仍然稀缺。在此，我们报告了通过还原具有庞大烷基保护基团的四溴二硅烷合成的可分离的NHC配位的NHC二烷基二硅亚乙烯基1。多核NMR光谱，高分辨率质谱，元素分析和X射线衍射分析相结合，充分表征了图1的结构。紫外可见光谱和DFT计算表明，1具有一个Si═Si双键，并且在末端Si原子上具有由NHC配位的孤对电子。1与N ₂ O和B（C ₆ F₅）₃提供由路易斯碱和路易斯酸（4）稳定的乙内酯的硅类似物。

更新日期：2021-04-12

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