Microwave irradiation promoted the intramolecular cycloaddition of 2-azidoacetamides derived from α-chiral propargylic amines, affording 1,4,5-trisubstituted triazoles 4 bearing a chiral aminomethyl side chain at C5. In contrast, for the same substrates 3a-k, Cu(I)-NHC complexes catalyzed the intermolecular cycloaddition in an unexpected desilylative fashion, leading to 1,4-disubstituted triazoles 5. This demonstrates that 1-silyl alkynes can be employed as substrates for CuAAC with a suitable coupling partner.
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Xia et al. (2014) studied this question.
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