Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 21, Issue 10, Pages 3924-3928Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201405829
Keywords
organotrifluoroborates; positron emission tomography; solvolysis; Suzuki-Miyaura cross coupling
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Funding
- NSERC
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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 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.
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