Abstract
Starting from commercially available 2-(chloromethyl)-allyltrimethylsilane, the corresponding 2-(azidomethyl)allylsilane was prepared through reaction with NaN<sub>3</sub>. 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 BCl<sub>3</sub>-mediated reaction with aromatic aldehydes.
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