Fusing Dicarbollide Ions with N-Heterocyclic Carbenes,Angewandte Chemie International Edition

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Fusing Dicarbollide Ions with N-Heterocyclic Carbenes
Angewandte Chemie International Edition ( IF 16.1 ) Pub Date : 2017-07-17 06:50:26 , DOI: 10.1002/anie.201705857
Jess Estrada ₁ , Vincent Lavallo ₁

Affiliation

Discovered by Hawthorne in 1965, dicarbollide ions are an intriguing class of nido-carboranes that mimic the behavior of the cyclopentadienyl anion. Herein, we show that it is possible to directly link the dicarbollide ion to an N-heterocyclic carbene (NHC) to form an isolable N-dicarbollide-substituted NHC dianion. This molecule can be accessed by the sequential double deprotonation of a mono-nido-carboranyl imidazolium zwitterion. As revealed by a single-crystal X-ray diffraction study, the first deprotonation leads to a monoanionic dicarbollide ion that adopts a bis(dicarbollide) structure in the solid state. Subsequent deprotonation of this monoanion leads to the first N-dicarbollide NHC, which was fully characterized by multinuclear NMR spectroscopy as well as single-crystal X-ray diffraction.

中文翻译：

将双糖类离子与N-杂环卡宾融合

霍索恩（Hawthorne）于1965年发现了双糖类离子，它是一类引人入胜的Nido- carboranes，它模仿环戊二烯基阴离子的行为。在本文中，我们表明可以将双糖脂离子直接连接到N-杂环卡宾（NHC）形成可分离的N-二糖脂取代的NHC二价阴离子。该分子可通过单-氨基的连续双去质子化而获得-碳硼烷基咪唑两性离子。正如单晶X射线衍射研究所揭示的那样，第一次去质子化导致单阴离子双糖脂离子在固态下采用双（双糖脂）结构。随后使该单阴离子去质子化，生成了第一个N-二咔唑NHC，其特征在于多核NMR光谱以及单晶X射线衍射。

更新日期：2017-07-17

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