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 approxim...

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Published inJournal of organic chemistry Vol. 73; no. 12; pp. 4662 - 4670
Main Authors Ting, Richard, Harwig, Curtis W, Lo, Justin, Li, Ying, Adam, Michael J, Ruth, Thomas J, Perrin, David M
Format Journal Article
LanguageEnglish
Published United States 20.06.2008
Subjects
Autoradiography
Boron Compounds - chemistry
Positron-Emission Tomography
Solubility
Water - chemistry
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Summary: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.
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ISSN:0022-3263
DOI:10.1021/jo800681d