Reaction of imidazole derivatives with trifluoromethylated arylacetylenes

• Nucleophilic addition of imidazoles to CF3-acetylenes leads to Z-isomers.
• Mixture of β- and α- vinylated imidazoles and benzimidazoles is formed.
• Not high polarization of the triple bond in CF3-acetylenes was revealed.
• Novel perspective multi-purpose building blocks were prepared.

The nucleophilic addition of imidazole derivatives to trifluoromethylated acetylenes was studied. Unpredictable regioselectivity of the reaction was observed to yield both β- and α-addition products. The reaction is 100% stereoselective to give the corresponding adducts as a Z-isomers only. The observed regioselectivity is discussed in terms of polarization of triple bond using experimental and calculated data.

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