(31)P NMR experiments revealed rapid decomposition of the Ph(3)PAu(+)TfO(-) complex in the presence of the furan-yne, which resulted in poor reactivity as reported in the literature. Therefore, instead of tuning different ligands (PR(3)), the 1,2,3-triazole was applied as a special X-factor to stabilize the catalyst. The desired phenol products were prepared in excellent yields (1% cat. up to 95% yield) and chemoselectivity (>20:1).
Efficient post-triazole regioselective N-2 arylation was developed from C-4, C-5 disubstituted-1,2,3-NH-triazoles. Three different approaches had been investigated, including S(N)Ar, Cu(I) catalyzed aryl amidation and Cu(II) mediated boronic acid coupling. The N-2-aryl triazoles were successfully synthesized with excellent yields. The structures were characterized by X-ray crystallography and some N-2-triazole products gave strong fluorescence with various emission controlled by the C-5 groups.
The FeCl(3)-catalyzed triazole propargylation was developed. This transformation was suitable for a large scope of substituted propargyl alcohols, giving the corresponding propargyl triazoles in excellent yields (up to 96%). Further derivatization produced the 1,1-bis-triazoles in excellent yields and regioselectivity, which could be applied as potential transition metal ligands or new reagents.
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