Fig. 4: Substrate scope of aryl azoles and electrophiles. | Nature Communications

Fig. 4: Substrate scope of aryl azoles and electrophiles.

From: Regioselective functionalization of aryl azoles as powerful tool for the synthesis of pharmaceutically relevant targets

Fig. 4: Substrate scope of aryl azoles and electrophiles.The alternative text for this image may have been generated using AI.

a Metalation of various aryl triazole derivatives and scope of the subsequent palladium-catalyzed cross-coupling. [a]Metalation yields were determined by 1H-NMR analysis of D2O-quenched reaction aliquots. Metalation time in brackets. [b]All yields refer to isolated compounds. [c]No metalation at the heterocycle was observed. [d]Performing the reaction with TMPLi exclusively led to metalation of the azole moiety. b Trapping of magnesium reagent 3a with various electrophiles. [e]I2 (4.3 equiv). [f]Metalation of 2a with Bu2Mg (vide infra), then I2 (4.3 equiv). [g]Benzaldehyde (2.5 equiv). [h]MeSSO2Me (2.5 equiv). [i]Transmetalation with CuCN•2LiCl (3.0 equiv), then benzoyl chloride (2.5 equiv). [j]Transmetalation with CuCN•2LiCl (3.0 equiv), then ethyl 2-(bromomethyl)acrylate (2.5 equiv).

Back to article page