Substituent effects on aryltrifluoroborate solvolysis in water: implications for Suzuki-Miyaura coupling and the design of stable [super 18]F-labeled aryltrifluoroborates for use in PET imaging

The results from a Hammett analysis of the solvolytic lability of aryltrifluoroborates where log([k.sub.solv]) values correlate to [sigma] values with a [rho] value of approximately -1, is presented. The data obtained provide insight for tuning the reactivity of boron for several uses including [super 18]F-labeled PET reagents and mechanistic implications for ArB[F.sub.3]-enhanced ligandless metal-mediated cross coupling reactions with aryltrifluoroborates.