3-butyl-1-(pyridin-2-yl)-1H-imidazol-3-ium tetrafluoroborate | 468082-01-1

• 英文名称: 3-butyl-1-(pyridin-2-yl)-1H-imidazol-3-ium tetrafluoroborate
• CAS: 468082-01-1
• 化学式: BF₄*C₁₂H₁₆N₃
• 分子量: 289.084
• InChiKey: OGQRVIONOPOAEN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
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• 重原子数：
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• 可旋转键数：
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• 环数：
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• sp3杂化的碳原子比例：
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• 拓扑面积：
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• 氢给体数：
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• 氢受体数：
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反应信息

• 作为反应物：
  描述：

  IrH5(PPh3)2 、 3-butyl-1-(pyridin-2-yl)-1H-imidazol-3-ium tetrafluoroborate 在 air 作用下， 以 四氢呋喃 为溶剂， 以58%的产率得到(η2-C,N)(N-butyl-N'-(2-pyridyl)imidazolidine-4-ylidene)bis(hydrido)bis(triphenylphosphine)iridium(III) tetrafluoroborate
  参考文献：
  名称：

  Abnormal Ligand Binding and Reversible Ring Hydrogenation in the Reaction of Imidazolium Salts with IrH₅(PPh₃)₂

  摘要：

  We show that imidazolium salts do not always give normal or even aromatic carbenes on metalation, and the chemistry of these ligands can be much more complicated than previously thought. N,N'-disubstituted imidazolium salts of type [(2-py)(CH2)(n)(C3H3N2)R]BF4 react with IrH5(PPh3)(2) to give N,C-chelated products (n = 0, 1; 2-py = 2-pyridyl; C(3)H(3)N2 = imidazolium; R = mesityl, n-butyl, i-propyl, methyl). Depending on the circumstances, three types of kinetic products can be formed: in one, the imidazole metalation site is the normal C2 as expected; in another, the metalation occurs at the abnormal C4 site; and in the third, C4 metalation is accompanied by hydrogenation of the imidazolium ring. The bonding mode is confirmed by structural studies, and spectroscopic criteria can also distinguish the cases. Initial hydrogen transfer can take place from the metal to the carbene to give the imidazolium ring hydrogenation product, as shown by isotope labeling; this hydrogen transfer proves reversible on reflux when the abnormal aromatic carbene is obtained as final product. Care may therefore be needed in the future in verifying the structure(s) formed in cases where a catalyst is generated in situ from imidazolium salt and metal precursor.

  DOI：

  10.1021/ja026735g