Investigation of Iodonium Trifluoroborate Zwitterions as Bifunctional Arene Reagents,Organic Letters

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Investigation of Iodonium Trifluoroborate Zwitterions as Bifunctional Arene Reagents
Organic Letters ( IF 4.9 ) Pub Date : 2017-11-16 00:00:00 , DOI: 10.1021/acs.orglett.7b03307
Raphaël Robidas ₁ , Vincent Guérin ₁ , Laurent Provençal ₁ , Marco Echeverria ₁ , Claude Y. Legault ₁

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The synthesis of a new family of iodonium zwitterions, in which the formal anion is a trifluoroborate moiety, is reported. These reagents present very good stability and have high resistance toward benzyne formation. Their structures were confirmed by X-ray crystallographic analysis and were further investigated using DFT calculations. QTAIM analysis supports an ionic, noncovalent, I⁺···BF₃^– interaction, in accordance with a true zwitterionic nature. Preliminary results of synthetic applications, the arylation of phenolates and trifluoroborate group functionalization, are reported.

中文翻译：

三氟硼酸碘鎓两性离子作为双功能芳烃试剂的研究

据报道，合成了一个新的碘鎓两性离子家族，其中形式阴离子为三氟硼酸酯部分。这些试剂具有非常好的稳定性，并且对苯并炔的形成具有很高的抵抗力。X射线晶体学分析证实了它们的结构，并使用DFT计算对其进行了进一步研究。QTAIM分析支持的离子，共价的，我⁺ ... BF ₃^-相互作用，按照本发明的真实性质两性离子。报告了合成应用的初步结果，酚盐的芳基化和三氟硼酸酯基团的官能化。

更新日期：2017-11-16

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