From Minutes to Years: Predicting Organotrifluoroborate Solvolysis Rates

Organotrifluoroborates solvolyze in water at rates that vary over five orders of magnitude. The negative logarithm of the solvolytic rate constant, pk((B-F)), correlates exceptionally well with the pK(a) of the analogous carboxylic acid (R-2 = 0.984). This unforeseen correlation may be of predictive value for several applications including Suzuki-Miyaura cross-coupling reactions and the design of F-18-organotrifluoroborate radioprosthetic groups.