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Mechanistic Study of the Fluoride-Induced Activation of a Kobayashi Precursor: Pseudo-SN2 Pathway via a Pentacoordinated Silicon Ate Complex
European Journal of Organic Chemistry ( IF 2.8 ) Pub Date : 2017-11-15 06:45:26 , DOI: 10.1002/ejoc.201701249
Song Liu 1 , Yang Li 1 , Yu Lan 1
Affiliation  

Density functional theory calculations reveal that activation of the Kobayashi aryne precursor consists of pseudo-SN2-type attack of the fluoride ion at the silicon atom, aryl–Si bond cleavage, and irreversible triflate (OTf) dissociation. The rate-determining step is determined to be addition of the fluoride ion to the trimethylsilyl group.

中文翻译:

氟化物诱导的小林前体活化的机理:通过五配位硅酸酯络合物的伪SN2途径。

密度泛函理论计算显示小林芳炔前体的活化由伪S的Ñ在硅原子上的氟离子的2型攻击,芳基-Si键的裂解,和不可逆的三氟甲磺酸酯(- OTF)解离。确定速率的步骤是将氟离子加成到三甲基甲硅烷基上。
更新日期:2017-11-15
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