title: From minutes to years: predicting organotrifluoroborate solvolysis rates.
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.
authors: Chemistry Department, 2036 Main Mall, University of British Columbia, Vancouver, BC, V6T 1Z1 (Canada).
authors: Zhibo
authors: Z
authors: Liu
authors: Daniel
authors: D
authors: Chao
authors: Ying
authors: Y
authors: Li
authors: Richard
authors: R
authors: Ting
authors: Jihyoon
authors: J
authors: Oh
authors: David M
authors: DM
authors: Perrin
mesh_terms: D001881:Borates / Q000737:chemistry*; D002264:Carboxylic Acids / Q000737:chemistry*; D003432:Cross-Linking Reagents / Q000737:chemistry; D005462:Fluorine Radioisotopes / Q000737:chemistry*; D012995:Solubility; D014867:Water
chemical_list: D001881:Borates; D002264:Carboxylic Acids; D003432:Cross-Linking Reagents; D005462:Fluorine Radioisotopes; D014867:Water
keywords: Suzuki-Miyaura cross coupling; organotrifluoroborates; positron emission tomography; solvolysis