Base-Promoted Protodeboronation of 2,6-Disubstituted Arylboronic Acids
Base-Promoted Protodeboronation of 2,6-Disubstituted Arylboronic Acids
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DOI：
10.1021/jo500734z
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发表时间：
2014-06-06
影响因子：
3.6
通讯作者：
Perrin, David M.
中科院分区：
文献类型：
--
作者：
Lozada, Jerome;Liu, Zhibo;Perrin, David M.
研究了含两个邻位吸电子基（EWG）取代基的硼酸芳酯的易变基促波化反应。在30种代表性硼酸盐中，只有二邻位取代的硼酸盐在水碱性条件下（200mm氢氧化物）容易发生C-B裂变。这些结果为交叉偶联反应、同位素标记的区域选择性氘化/氚化以及新型f -18三氟硼酸盐放射性修复术的设计提供了基本的解析机制。
Facile based promoted deboronation of electron-deficient arylboronate esters was observed for arylboronates containing two ortho electron-withdrawing group (EWG) substituents. Among 30 representative boronates, only the diortho-substituted species underwent facile C-B fission in aqueous basic conditions (200 mM hydroxide). These results provide fundamental insight into deboronative mechanisms with implications for cross-coupling reactions, regioselective deuteration/tritiation for isotopic labeling, and the design of new F-18-trifluoroborate radioprosthetics.