Substituent effects on aryltrifluoroborate solvolysis in water:: Implications for Suzuki-Miyaura coupling and the design of stable 18F-labeled aryltrifluoroborates for use in PET imaging
Substituent effects on aryltrifluoroborate solvolysis in water:: Implications for Suzuki-Miyaura coupling and the design of stable 18F-labeled aryltrifluoroborates for use in PET imaging
复制标题
DOI：
10.1021/jo800681d
复制
发表时间：
2008-06-20
影响因子：
3.6
通讯作者：
Perrin, David M.
中科院分区：
文献类型：
--
作者：
Ting, Richard;Harwig, Curtis W.;Perrin, David M.
而吸电子取代基延迟芳基三氟硼酸盐溶剂分解的速率，给电子基团增强it.here提出了一个Hammett分析的芳基三氟硼酸盐的溶剂分解不稳定性，其中log（k（solv））值相关的σ值与ρ值约为-1。这项工作提供了一个可预测的规则，调整硼的反应性，包括F-18标记的PET试剂的几种用途，并具有机械的影响ArBF 3增强无配体金属介导的交叉偶联反应与芳基三氟硼酸酯。
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.