(4-fluorophenyl)cycloheptane | 1146593-98-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (4-fluorophenyl)cycloheptane
• CAS: 1146593-98-7
• 化学式: C₁₃H₁₇F
• 分子量: 192.276
• InChiKey: LQDOPLCEUPCFCX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  溴代环庚烷 、 di(4-fluorophenyl)zinc 在 Fe(dpbz)₂Br 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 3.0h， 以99%的产率得到(4-fluorophenyl)cycloheptane
  参考文献：
  名称：

  Iron(I) in Negishi Cross-Coupling Reactions

  摘要：

  Herein we demonstrate both the importance of Fe(I) in Negishi cross-coupling reactions with arylzinc reagents and the isolation of catalytically competent Fe(I) intermediates. These complexes, [FeX-(dpbz)(2)] [X = 4-tolyl (7), Cl (8a), Br (8b); dpbz = 1,2-bis(diphenylphosphino)benzene], were characterized by crystallography and tested for activity in representative reactions. The complexes are low-spin with no significant spin density on the ligands. While complex 8b shows performance consistent with an on-cycle intermediate, it seems that 7 is an off-cycle species.

  DOI：

  10.1021/ja303250t

文献信息

• The first iron-catalysed aluminium-variant Negishi coupling: critical effect of co-existing salts on the dynamic equilibrium of arylaluminium species and their reactivity
  作者：Shintaro Kawamura、Kentaro Ishizuka、Hikaru Takaya、Masaharu Nakamura

  DOI：10.1039/c0cc01216e

  日期：——

  The first example of an iron-catalysed Negishi coupling between arylaluminium reagents and alkyl halides illustrates that the co-existing salts highly influence the dynamic equilibrium of the organoaluminium species, and have a critical effect on the reactivity and selectivity of the coupling reaction.

  第一个铁催化的Negishi偶联反应示例，即芳基铝试剂与烷基卤化物的反应，表明共存的盐类对有机铝物种的动态平衡产生强烈影响，并对此偶联反应的活性和选择性具有关键作用。
• Iron-catalysed fluoroaromatic coupling reactions under catalytic modulation with 1,2-bis(diphenylphosphino)benzene
  作者：Takuji Hatakeyama、Yoshiyuki Kondo、Yu-ichi Fujiwara、Hikaru Takaya、Shingo Ito、Eiichi Nakamura、Masaharu Nakamura

  DOI：10.1039/b820879d

  日期：——

  A catalytic amount of 1,2-bis(diphenylphosphino)benzene (DPPBz) achieves selective cleavage of sp3-carbon–halogen bond in the iron-catalysed cross-coupling between polyfluorinated arylzinc reagents and alkyl halides, which was unachievable with a stoichiometric modifier such as TMEDA; the selective iron-catalysed fluoroaromatic coupling provides easy and practical access to polyfluorinated aromatic compounds.

  在铁催化下，通过多氟代芳基锌试剂与烷基卤化物的交叉耦合反应中，仅使用催化量的1,2-双(二苯基膦)苯（DPPBz）就能实现sp3碳-卤素键的选择性断裂，而使用TMEDA等化学计量修饰剂时这一反应是难以实现的；这种选择性的铁催化氟代芳香族耦合反应为制备多氟代芳香化合物提供了简便实用的途径。
• Iron(ii) complexes with functionalized amine-pyrazolyl tripodal ligands in the cross-coupling of aryl Grignard with alkyl halides
  作者：Fei Xue、Jin Zhao、T. S. Andy Hor

  DOI：10.1039/c1dt10258c

  日期：——

  Structurally distinctive Fe(II) complexes with furan, thiophene and pyridine functionalized amine-pyrazolyl tripodal hybrid ligands have been synthesized and crystallographically characterized. The tether substituent at the central amine plays an active role in determining the coordination mode of the ligand and the metal geometry. All complexes are catalytically active towards cross-coupling of aryl Grignard reagents with primary and secondary alkyl halides with β-hydrogen under ambient conditions. ESI-MS spectra analysis revealed the ligand-stabilised Fe(II) and Mg(II) species.

  具有结构特征的Fe(II)配合物与功能化氨基-呋喃、噻吩和吡啶的三齿混合配体合成并通过晶体学进行表征。中央氨基的连接取代基在确定配体的配位模式和金属几何形状方面发挥了积极作用。所有配合物在环境条件下对芳基格氏试剂与带有β-氢的初级和次级卤代烷的交叉偶联反应均表现出催化活性。ESI-MS光谱分析揭示了配体稳定的Fe(II)和Mg(II)物种。