title: Substituent effects on aryltrifluoroborate solvolysis in water: implications for Suzuki-Miyaura coupling and the design of stable (18)F-labeled aryltrifluoroborates for use in PET imaging.
abstract: Whereas electron withdrawing substituents retard the rate of aryltrifluoroborate solvolysis, electron-donating groups enhance it. Herein is presented a Hammett analysis of the solvolytic lability of aryltrifluoroborates where log(k(solv)) values correlate to sigma values with a rho value of approximately -1. This work provides a predictable rubric for tuning the reactivity of boron for several uses including (18)F-labeled PET reagents and has mechanistic implications for ArBF(3)-enhanced ligandless metal-mediated cross coupling reactions with aryltrifluoroborates.
authors.affiliation: Chemistry Department, University of British Columbia, and TRIUMF, Vancouver, BC, Canada.
authors.forename: Richard
authors.initials: R
authors.lastname: Ting
authors.forename: Curtis W
authors.initials: CW
authors.lastname: Harwig
authors.forename: Justin
authors.initials: J
authors.lastname: Lo
authors.forename: Ying
authors.initials: Y
authors.lastname: Li
authors.forename: Michael J
authors.initials: MJ
authors.lastname: Adam
authors.forename: Thomas J
authors.initials: TJ
authors.lastname: Ruth
authors.forename: David M
authors.initials: DM
authors.lastname: Perrin
mesh_terms: D001345:Autoradiography; D001896:Boron Compounds / Q000737:chemistry*; D049268:Positron-Emission Tomography; D012995:Solubility; D014867:Water / Q000737:chemistry*
chemical_list: D001896:Boron Compounds; D014867:Water