3-butyl-1-(1,10-phenanthrolin-2-yl)imidazolylidene hexafluorophosphate | 1114572-58-5

• 英文名称: 3-butyl-1-(1,10-phenanthrolin-2-yl)imidazolylidene hexafluorophosphate
• 英文别名: 3-n-butyl-1-(1,10-phenanthrolin-2-yl)imidazolium hexafluorophosphate；3-butyl-1-(1,10-phenanthrolin-2-yl)imidazolium hexafluorophosphate；[N-butyl-N-(1,10-phenanthrolin-2-yl)imidazolium]PF6；[HL2][PF6]
• CAS: 1114572-58-5
• 化学式: C₁₉H₁₉N₄*F₆P
• 分子量: 448.351
• InChiKey: JQQDWALFFURPJZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  None
• 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：
  None

反应信息

• 作为反应物：
  描述：

  bis(triphenylphosphine)nickel(II) chloride 、 3-butyl-1-(1,10-phenanthrolin-2-yl)imidazolylidene hexafluorophosphate 在 silver(l) oxide 作用下， 以 乙腈 为溶剂， 以37%的产率得到chloro(3-n-butyl-1-(1,10-phenanthrolin-2-yl)imidazolylidene)nickel(II) hexafluorophosphate
  参考文献：
  名称：

  Pincer Complexes of Palladium- and Nickel-Containing 3-Butyl-1-(1,10-phenanthrolin-2-yl)imidazolylidene as Efficient Aqueous Sonogashira and Kumada Coupling Reactions

  摘要：

  Palladium and nickel complexes, [Pd(L)Cl](PF6) (1), [Ni(L)Cl](PF6) (2), and [Ni(L)(2)](PF6)(2) (3), containing 3-butyl-1-(1,10-phenanthrolin-2-yl)imidazolylidene (L) have been synthesized and fully characterized by NMR and EST-MS spectroscopy and X-ray diffraction analysis. The unsymmetrical NNC pincer complexes 1 and 2 are square planar with a chloride trans to the internal nitrogen atom of phenanthroline. Complex 3 is a paramagnetic octahedral complex with its central metal surrounded by two pincer ligands. A catalytic study shows that palladium compound 1 is highly active in copper-free Sonogashira cross-coupling reactions of aryl iodides at room temperature and aryl bromides at 80 degrees C in neat water. The nickel complex 2 exhibits good activity in the Kumada cross-coupling reaction of aryl chloride at room temperature.

  DOI：

  10.1021/om801056v

文献信息

• Synthesis, structures, and properties of ruthenium(<scp>ii</scp>) complexes of N-(1,10-phenanthrolin-2-yl)imidazolylidenes
  作者：Shaojin Gu、Bo Liu、Jiuxi Chen、Huayue Wu、Wanzhi Chen

  DOI：10.1039/c1dt11269d

  日期：——

  Mononuclear ruthenium complexes [RuCl(L1)(CH3CN)2](PF6) (2a), [RuCl(L2)(CH3CN)2](PF6) (2b), [Ru(L1)(CH3CN)3](PF6)2 (4a), [Ru(L2)(CH3CN)3](PF6)2 (4b), [Ru(L2)2](PF6)2 (5), [RuCl(L1)(CH3CN)(PPh3)](PF6) (6), [RuCl(L1)(CO)2](PF6) (7), and [RuCl(L1)(CO)(PPh3)](PF6) (8), and a tetranuclear complex [Ru2Ag2Cl2(L1)2(CH3CN)6](PF6)4 (3) containing 3-(1,10-phenanthrolin-2-yl)-1-(pyridin-2-ylmethyl)imidazolylidene (L1) and 3-butyl-1-(1,10-phenanthrolin-2-yl)imidazolylidene (L2) have been prepared and fully characterized by NMR, ESI-MS, UV-vis spectroscopy, and X-ray crystallography. Both L1 and L2 act as pincer NNC donors coordinated to ruthenium (II) ion. In 3, the Ru(II) and Ag(I) ions are linked by two bridging Cl− through a rhomboid Ag2Cl2 ring with two Ru(II) extending to above and down the plane. Complexes 2–8 show absorption maximum over the 354–428 nm blueshifted compared to Ru(bpy)32+ due to strong σ-donating and weak π-acceptor properties of NHC ligands. Electrochemical studies show Ru(II)/Ru(III) couples over 0.578–1.274 V.

  单核铑复杂物 [RuCl(L1)(CH3CN)2](PF6) (2a)、[RuCl(L2)(CH3CN)2](PF6) (2b)、[Ru(L1)(CH3CN)3](PF6)2 (4a)、[Ru(L2)(CH3CN)3](PF6)2 (4b)、[Ru(L2)2](PF6)2 (5)、[RuCl(L1)(CH3CN)(PPh3)](PF6) (6)、[RuCl(L1)(CO)2](PF6) (7) 和 [RuCl(L1)(CO)(PPh3)](PF6) (8)，以及一个含有 3-(1,10-菲啰啉-2-基)-1-(吡啶-2-基甲基)咪唑烯 (L1) 和 3-丁基-1-(1,10-菲啰啉-2-基)咪唑烯 (L2) 的四核复杂物 [Ru2 L2(L1)2(CH3CN)6](PF6)4 (3) 已被合成并通过 NMR、ESI-MS、紫外-可见光光谱和 X 射线晶体学进行充分表征。L1 和 L2 作为夹心 NNC 配体与铑(II)离子配位。在 3 复杂物中，Ru(II) 和 Ag(I) 离子通过两个桥联 Cl− 相连，形成一个菱形 Ag2Cl2 href=https://www.molaid.com/MS_3163 target="_blank">L2 环，两个 Ru(II) 离子分别延伸到平面上方和下方。复杂物 2–8 相较于 Ru(bpy)32+ 显示出 354–428 nm 的蓝移吸收峰，原因是 NHC 配体具有强 σ 供体和弱 π 受体特性。电化学研究显示 Ru(II)/Ru(III) 对的电位范围为 0.578–1.274 V。
• Platinum(ii) complexes with polydentate N-heterocyclic carbenes: synthesis, structural characterization and hydrosilylation catalysis
  作者：Chunxin Lu、Shaojin Gu、Wanzhi Chen、Huayu Qiu

  DOI：10.1039/b924587a

  日期：——

  The platinum(II) complexes of multidentate N-heterocyclic carbenes, [Pt(L1)2Cl](PF6) (1, L1 = N-methyl-N-(2-pyrimidinyl)imidazolylidene), [Pt(L2)Cl](PF6) (2, L2 = N-butyl-N-(1,10-phenanthrolin-2-yl)imidazolylidene), [PtL3](PF6)2 (3, L3 = bis(N-picolylimidazolylidenyl)methane), [PtL4](PF6)2 (4, L4 = (bis(N-2-pyrimidylimidazolylidenyl)methane) (4) and [Pt(L5)2](PF6)2 [5, L5 = bis(N-pyridylimidazoliumyl)methane] have been synthesized and structurally characterized. All these complexes exhibit slightly distorted square-planar configuration. These complexes are efficient catalyst precursors for hydrosilylation of alkynes. Complexes 2 and 4 are much more active than complexes 1, 3 and 5. In the hydrosilylation of arylacetylenes, relatively long induction periods were observed for 1, 3 and 5.

  多齿 N-杂环碳烯的铂(II)配合物，[Pt(L1)2Cl](PF6) (1, L1 = N-甲基-N-(2-嘧啶基)咪唑亚基)，[Pt(L2)Cl](PF6) (2, L2 = N-丁基-N-(1,10-菲罗啉-2-基)咪唑亚基)，[PtL3](PF6)2 (3、4）和 [Pt(L5)2](PF6)2 [5, L5 = 双（N-吡啶基咪唑鎓）甲烷]。所有这些复合物都呈现出略微扭曲的方平面构型。这些配合物是炔烃氢化的高效催化剂前体。络合物 2 和 4 的活性远高于络合物 1、3 和 5。在芳基乙炔的氢硅化过程中，1、3 和 5 的诱导期相对较长。
• Dinuclear Copper(I) Complexes of Phenanthrolinyl-Functionalized NHC Ligands
  作者：Bo Liu、Congyan Chen、Yuejiao Zhang、Xiaolong Liu、Wanzhi Chen

  DOI：10.1021/om400738c

  日期：2013.10.14
• Carbene Transfer Reactivities of Nickel(II)–N-Heterocyclic Carbene Complexes and Their Applications in the Synthesis of Metal–NHC Complexes
  作者：Bo Liu、Xiaolong Liu、Chao Chen、Congyan Chen、Wanzhi Chen

  DOI：10.1021/om200881s

  日期：2012.1.9

  We describe a new synthetic procedure for transition-metal N-heterocyclic carbene complexes A number of Pd(II), Pt(II), Co(III), and Ru(II) complexes containing functionalized NHCs have been obtained in good to excellent yields using Ni-II-NHC complexes as carbene transfer reagents. Ni-II-NHC complexes are easily prepared from the direct reactions of the corresponding imidazolium salts with commercially available Raney nickel powder. The byproduct of transmetalation reactions, NiCl2, can be easily removed by simple filtration. This study offers a new, economical, and practical synthetic method for metal-NHC complexes.