In recent years, significant progress has been made in the development of transition metal-catalyzed fluorination methods, and in particular, a great emphasis has been placed on the use of electrophilic fluorinating reagents in conjunction with metal catalysts. Understanding the mechanism of metal-catalyzed fluorinations would be of considerable importance for the optimization of existing methods, expansion of substrate scope, enhancement of chemoselectivity, as well as the development of new synthetic reactions. The recent development of a silver-catalyzed decarboxylative fluorination reaction using F-TEDA-BF4 is of significant importance due to its procedural ease, mild reaction conditions, and extensive substrate scope.1 A series of kinetic and spectroscopic studies have been performed on the Ag(I)/ F-TEDA-BF4-mediated reaction. Kinetic data show that the reaction is approximately first order in silver and F-TEDA-BF4, and inverse order in carboxylic acid. The relationship of the kinetic data to possible mechanisms will be described. 1. Yin, F.; Wang, Z.; Li, Z.; Li, C. J. Am. Chem. Soc. 2012, 134, 10401–10404.

On the mechanism of silver-catalyzed decarboxylative fluorination

249th National Meeting (2015)

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