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An Alternative Method for the Synthesis of N-Pentafluorophenyl Triazolium Salts.

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A route for the synthesis of 1,2,4-triazolium salts via oxidation of a thione precursor is demonstrated. N-Pentafluorophenyl-substituted salts are produced in 20-63% overall yields. Isolation and purification of the azolium… Click to show full abstract

A route for the synthesis of 1,2,4-triazolium salts via oxidation of a thione precursor is demonstrated. N-Pentafluorophenyl-substituted salts are produced in 20-63% overall yields. Isolation and purification of the azolium salts are simplified compared to the traditional synthetic route. Late-stage selection of the counterion allows the synthesis of a variety of salts from a parent thione. The salts have been compared in Stetter and cross-benzoin reactions with an appreciable counterion effect in both reactions.

Keywords: triazolium salts; method synthesis; alternative method; synthesis; synthesis pentafluorophenyl

Journal Title: Organic letters
Year Published: 2022

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