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Reactions of the dipolarophile (trimethylsilyl)acetylene with a number of aryl 1a - f and heteroaryl azides 1g - i have been examined as routes to the 1-aryl (or 1-heteroaryl) trimethylsilyl-1,2,3-triazoles 2a - i. Regioselectivity that privileges the formation of the corresponding C-4 silylated triazoles, over the C-5 ones was observed in all instances. The regiochemistry of the C-4 adducts was established by 1 H-, 13 C-NMR spectroscopy and confirmed by X-ray crystallography of the 2,2,2-trifluoro-1-{5-(4-(trimethylsilyl)-1H-1,2,3-triazol-1-yl)-2- thienyl}-1-ethanone 2i and 1-phenyl-4-(trimethylsilyl)-1H-triazole 2l.

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New insight on the cycloaddition of aryl and heteroaryl azides with (trimethylsilyl)acetylene. Spectroscopic and x-ray crystallographic data of silylated 1,2,3-triazoles