Journal of the American Chemical Society 2006-08-02

Oxidation of hydroxyl-substituted organotrifluoroborates.

Gary A Molander, Daniel E Petrillo

Index: J. Am. Chem. Soc. 128 , 9634, (2006)

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Abstract

Potassium- and tetra-n-butylammonium organotrifluoroborates containing hydroxyl groups have been prepared and oxidized using several common oxidants. Aryl-, alkenyl-, and alkyltrifluoroborates containing both primary and secondary hydroxyl groups were oxidized in moderate to excellent yields with complete retention of the trifluoroborate moiety. The utility of these oxidized products was demonstrated in a Suzuki-Miyaura cross-coupling reaction.