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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.
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Liu et al. (2015) studied this question.
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