Alkyl azides are prepared in good to excellent yields by treatment of alcohols, thiols and trimethylsilyl ethers with 2,4,6-trichloro[1,3,5]triazine/n-Bu4NN 3 in acetonitrile. This method is highly selective for conversion of primary alcohols to alkyl azides in the presence of secondary and tertiary alcohols, thiols and trimethysilyl ethers.
2,4,6-trichloro[1,3,5] triazine (TT); alcohol; thiol; trimethylsilyl ether; alkyl azide