硼氮吲哚的亲电芳香取代反应。
Electrophilic aromatic substitution of a BN indole.
机构信息
Department of Chemistry, University of Oregon, Eugene, Oregon 97403, United States.
出版信息
J Am Chem Soc. 2010 Nov 24;132(46):16340-2. doi: 10.1021/ja107312u. Epub 2010 Nov 2.
Abstract
We report the first examples of a "BN-fused" indole, and we demonstrate that this new family of unnatural indole derivatives undergoes electrophilic aromatic substitution (EAS) reactions with the same regioselectivity as its organic analogue. Competition experiments reveal that N-t-Bu-BN-indole is more nucleophilic in EAS reactions than its carbonaceous counterpart. X-ray structural analysis between BN indole and classic indole highlights significant differences in bond distances, in particular for bonds associated with the boron atom.
摘要
我们报告了首例“BN 融合”吲哚的例子，并证明这种新的非天然吲哚衍生物与有机类似物一样，经历亲电芳香取代（EAS）反应具有相同的区域选择性。竞争实验表明，N-t-Bu-BN-吲哚在 EAS 反应中的亲核性比其碳类似物更强。BN 吲哚和经典吲哚之间的 X 射线结构分析突出了键距离的显著差异，特别是与硼原子相关的键。
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