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.
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.
Ting
Richard
R
Chemistry Department, University of British Columbia, and TRIUMF, Vancouver, BC, Canada.
Harwig
Curtis W
CW
Lo
Justin
J
Li
Ying
Y
Adam
Michael J
MJ
Ruth
Thomas J
TJ
Perrin
David M
DM
D001345:Autoradiography; D001896:Boron Compounds / Q000737:chemistry*; D049268:Positron-Emission Tomography; D012995:Solubility; D014867:Water / Q000737:chemistry*
D001896:Boron Compounds; D014867:Water