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Updated: Jun 12, 2025

Metal-free Synthesis of Ynones from Acyl Chlorides and Potassium Alkynyltrifluoroborate Salts
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Copper-Catalyzed Oxidative Synthesis of 3-Aryl-5-fluoroalkyl-1,3,4-oxadiazol-2(3H)-ones Using Perfluorocarboxylic
Jiaqing Lu1,2, Shouxiong Chen1, Minze Wu1
1Fujian Provincial University Engineering Research Center of Green Materials and Chemical Engineering, and Fujian Engineering Research Center of New Chinese lacquer Material, College of Materials and Chemical Engineering, Minjiang University, Fuzhou 350108, China.
Abstract:
A copper-catalyzed oxidative annulation of sydnones with perfluorocarboxylic anhydride for the synthesis of 3-aryl-5-fluoroalkyl-1,3,4-oxadiazol-2(3H)-ones is developed. A diverse array of 3-aryl-5-fluoroalkyl-1,3,4-oxadiazol-2(3H)-ones are prepared with good yields (>73 examples, yields up to 95%). The synthetic utility of the developed protocol was demonstrated by gram-scale synthesis, and the synthetic transformation to 1,2,4-triazol-3-one products. A mechanistic study suggests that the reaction proceeds via the extrusion of carbon dioxide to generate the hydrazide intermediate, which then undergoes intramolecular cyclization and oxidation.
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