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1-(α-Aminoalkyl)benzotriazoles react with sodium dialkynyldiethylaluminates to give propargylic amines in excellent yields, including unsubstituted N,N-dialkyl propargylamines, which are difficult to obtain from lithium acetylide. The reaction of α-benzotriazolyl alkyl ethers and sodium dialkynyldiethylaluminate in the presence of zinc iodide also gives propargylic ethers in excellent yields. Unsubstituted propargyl ethers are prepared via the desilylation of trimethylsilylpropargyl ethers.

The radical addition reaction of alkyl iodides with alpha,beta-unsaturated esters, nitriles, and ketones proceeds in moderate to excellent yields (50-95%) using Ni(OAc)(2) (0.05-0.2 equiv)-BER (3-5 equiv) in methanol in 1-9 h at room temperature or at 65 degrees C. Nickel boride on borohydride exchange resin (BER) is a good alternative reagent to tributyltin hydride for the coupling of alkyl iodides with the electron deficient alkenes in methanol. Compared with tributyltin hydride method, this method has an advantage of simple workup, since nickel boride-BER can be removed readily by filtration.

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