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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

TitleSubstituent 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
Publication TypeJournal Article
Year of Publication2008
AuthorsTing, R, Harwig, CW, Lo, J, Li, Y, Adam, MJ, Ruth, TJ, Perrin, DM
JournalJournal of Organic Chemistry
Volume73
Pagination4662-4670
Date PublishedJun
Type of ArticleArticle
ISBN Number0022-3263
KeywordsAMINO-ACIDS, AROMATIC SUBSTITUTION, CHEMISTRY, CHYMOTRYPSIN, CONSTANTS, FLUORIDE, HYDROLYSIS, ORGANOBORON COMPOUNDS, POTASSIUM ARYL, TRIFLUOROMETHYL GROUP
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.

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