|Title||From minutes to years: predicting organotrifluoroborate solvolysis rates}|
|Publication Type||Journal Article|
|Year of Publication||2015|
|Authors||Liu, Z, Chao, D, Li, Y, Ting, R, Oh, J, Perrin, DM|
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 pKa 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 (18)F-organotrifluoroborate radioprosthetic groups.