Selective Generation of (1H-1,2,4-Triazol-1-yl)methyl Carbanion and Condensation with Carbonyl Compounds

2-(1H-1,2,4-Triazol-1-yl)ethanols have received significant interest in agricultural and medicinal chemistry owing to their herbicidal and antifungal activities. To develop a versatile method to access these substituted triazoles, we explored the generation of the (1H-1,2,4-triazol-1-yl)methyl carbanion and its condensation with carbonyl compounds. By judicious choice of a suitable anion precursor (tributylstannyl group) or a stabilizing anion group (phenylsulfanyl or phenylsulfinyl group), a wide range of aldehydes and ketones reacted with the carbanions to give a large diversity of 2-(1H-1,2,4-triazol-1-yl)ethanols in good yields.