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.
摘要：
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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关键词：
ORGANOBORON COMPOUNDS POTASSIUM ARYL AROMATIC SUBSTITUTION TRIFLUOROMETHYL GROUP AMINO-ACIDS HYDROLYSIS CHEMISTRY CONSTANTS FLUORIDE CHYMOTRYPSIN
DOI：
10.1021/jo800681d
被引量：
年份：
2008
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