@article {2288, title = {Substituent effects on aryltrifluoroborate solvolysis in water: Implications for Suzuki-Miyaura coupling and the design of stable F-18-labeled aryltrifluoroborates for use in PET imaging}, journal = {Journal of Organic Chemistry}, volume = {73}, number = {12}, year = {2008}, note = {ISI Document Delivery No.: 313RGTimes Cited: 17Cited Reference Count: 41Ting, Richard Harwig, Curtis W. Lo, Justin Li, Ying Adam, Michael J. Ruth, Thomas J. Perrin, David M.}, month = {Jun}, pages = {4662-4670}, type = {Article}, 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 F-18-labeled PET reagents and has mechanistic implications for ArBF3-enhanced ligandless metal-mediated cross coupling reactions with aryltrifluoroborates.}, keywords = {AMINO-ACIDS, AROMATIC SUBSTITUTION, CHEMISTRY, CHYMOTRYPSIN, CONSTANTS, FLUORIDE, HYDROLYSIS, ORGANOBORON COMPOUNDS, POTASSIUM ARYL, TRIFLUOROMETHYL GROUP}, isbn = {0022-3263}, url = {://000256757100038}, author = {Ting, R. and Harwig, C. W. and Lo, J. and Li, Y. and Adam,Michael J. and Ruth, T. J. and Perrin,David M.} } @article {2288, title = {Substituent effects on aryltrifluoroborate solvolysis in water: Implications for Suzuki-Miyaura coupling and the design of stable F-18-labeled aryltrifluoroborates for use in PET imaging}, journal = {Journal of Organic Chemistry}, volume = {73}, number = {12}, year = {2008}, note = {ISI Document Delivery No.: 313RGTimes Cited: 17Cited Reference Count: 41Ting, Richard Harwig, Curtis W. Lo, Justin Li, Ying Adam, Michael J. Ruth, Thomas J. Perrin, David M.}, month = {Jun}, pages = {4662-4670}, type = {Article}, 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 F-18-labeled PET reagents and has mechanistic implications for ArBF3-enhanced ligandless metal-mediated cross coupling reactions with aryltrifluoroborates.}, keywords = {AMINO-ACIDS, AROMATIC SUBSTITUTION, CHEMISTRY, CHYMOTRYPSIN, CONSTANTS, FLUORIDE, HYDROLYSIS, ORGANOBORON COMPOUNDS, POTASSIUM ARYL, TRIFLUOROMETHYL GROUP}, isbn = {0022-3263}, url = {://000256757100038}, author = {Ting, R. and Harwig, C. W. and Lo, J. and Li, Y. and Adam,Michael J. and Ruth, T. J. and Perrin,David M.} }