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From minutes to years: predicting organotrifluoroborate solvolysis rates}

TitleFrom minutes to years: predicting organotrifluoroborate solvolysis rates}
Publication TypeJournal Article
Year of Publication2015
AuthorsLiu, Z, Chao, D, Li, Y, Ting, R, Oh, J, Perrin, DM
JournalChemistry
Volume21
Pagination3924–3928
Date PublishedMar
Abstract

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.