Synthetic Applications of 2-(Azidomethyl)allyltrimethylsilane
Synthetic Applications of 2-(Azidomethyl)allyltrimethylsilane
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DOI：
10.1055/s-0032-1318144
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发表时间：
2013-03-01
期刊：
影响因子：
2
通讯作者：
Taddei, Maurizio
中科院分区：
文献类型：
--
作者：
Ferrini, Serena;Cini, Elena;Taddei, Maurizio
以市售的2-(氯甲基)-烯丙基三甲基硅烷为原料，通过与NaN3反应制备相应的2-(叠氮基甲基)烯丙基硅烷。该产物在分离和储存时稳定，可用于叠氮基与烯烃的热环加成，得到含烯丙基硅烷的三唑啉或氮丙啶。微波 (MW) 介电加热不会加速该反应，但叠氮化物片段会与一系列炔烃（包括炔酰胺）发生 MW 辅助的 Cu(I) 催化环加成反应。烯丙基硅烷与醛的路易斯酸介导的 Hosomi-Sakurai 反应也是可能的。通过一系列 Cu(I) 催化的叠氮化物环加成反应，在 MW 介电加热下以及 BCl3 介导的与芳香醛的反应，一锅法转化为不同的含三唑基高烯丙醇。
Starting from commercially available 2-(chloromethyl)-allyltrimethylsilane, the corresponding 2-(azidomethyl)allylsilane was prepared through reaction with NaN3. The product was stable upon isolation and storage and could be used for thermal cycloaddition of the azido group with alkenes to give allylsilane-containing triazolines or aziridines. This reaction was not accelerated by microwave (MW) dielectric heating, however, the azide fragment undergoes MW-assisted Cu(I)-catalyzed cycloaddition with a range of alkynes (including ynamides). Lewis acid mediated Hosomi-Sakurai reaction of the allylsilane with aldehydes was also possible. A one-pot transformation into different triazolo-containing homoallyl alcohols was carried out through a sequence of Cu(I)-catalyzed azide cycloaddition under MW dielectric heating and BCl3-mediated reaction with aromatic aldehydes.