4-fluoro-N-(1-phenylethyl)aniline

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 4-fluoro-N-(1-phenylethyl)aniline
• 英文别名: N-(4-Fluorophenyl)-alpha-phenethylamine
• 化学式: C₁₄H₁₄FN
• mdl: MFCD11145049
• 分子量: 215.27
• InChiKey: NASFPNSCUMQAOD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.142
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4-fluoro-N-(1-phenylethylidene)aniline 在 三乙基硅烷 、 [(η5-pentamethylcyclopentadienyl)Ir(2-phenylpyridine(1-))Cl] 、 四(3,5-二(三氟甲基)苯基)硼酸钠 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 以95%的产率得到4-fluoro-N-(1-phenylethyl)aniline
  参考文献：
  名称：

  Efficient hydrosilylation of imines using catalysts based on iridium(iii) metallacycles

  摘要：

  Ir（iii）金属环化合物被应用为催化剂，用于使用钠四(三，五-三氟甲基)苯基硼酸盐（NaBArF24）作为添加剂对酮亚胺和醛亚胺进行硅氢化反应。通过使用微量过量的有机硅烷试剂，反应在低催化剂负荷和室温下迅速高效地进行。

  DOI：

  10.1039/c4cy01233j

文献信息

• Fast Reductive Amination by Transfer Hydrogenation “on Water”
  作者：Qian Lei、Yawen Wei、Dinesh Talwar、Chao Wang、Dong Xue、Jianliang Xiao

  DOI：10.1002/chem.201204194

  日期：2013.3.18

  Reductive amination of various ketones and aldehydes by transfer hydrogenation under aqueous conditions has been developed, by using cyclometallated iridium complexes as catalysts and formate as hydrogen source. The pH value of the solution is shown to be critical for a high catalytic chemoselectivity and activity, with the best pH value being 4.8. In comparison with that in organic solvents, the reductive

  通过使用环金属化的铱络合物作为催化剂，甲酸盐作为氢源，开发了在水性条件下通过转移氢化进行各种酮和醛的还原胺化反应。溶液的pH值对于高催化化学选择性和活性至关重要，最佳pH值为4.8。与有机溶剂相比，水相中的还原胺化速度更快，并且底物与催化剂的摩尔比（S / C）可设置为高达1×10 5。，是还原胺化反应中报道的最高S / C值。该催化剂易于获得，反应操作简单，可以使各种酮和醛与各种胺高产率地反应。该方案为合成胺化合物提供了一种实用且环保的新方法。
• Simple, efficient and reusable Pd–NHC catalysts for hydroamination
  作者：Qian Chen、Lanlan Lv、Meng Yu、Yanhui Shi、Yuling Li、Guangsheng Pang、Changsheng Cao

  DOI：10.1039/c3ra42990c

  日期：——

  series of chelating NHC–palladium complexes with different alkane-bridges of the type Pd[NHC–(CH2)n–NHC]X2 (X = Br or Cl, n = 2–4) were synthesized, where NHC is a triazolyl-N-heterocyclic carbene donor ligand. The bromide complexes with n = 2 and 3 were characterized by X-ray crystallography. The effects of the length of the bridge and halide ligand on the catalytic reactivity in the hydroamination reaction

  合成了一系列具有不同Pd [NHC–（CH 2）n –NHC] X 2（X = Br或Cl，n = 2–4）烷烃桥的螯合NHC-钯配合物。三唑基-N-杂环卡宾供体配体。X射线晶体学表征n = 2和3的溴化物配合物。研究了桥键和卤化物配体的长度对加氢胺化反应催化活性的影响。丙烯桥式Pd-NHC溴化物配合物2观察到最佳的催化性能。的加氢胺化苯乙炔 或者 4-甲基苯基乙炔用2催化的各种取代苯胺仅以良好的收率产生了马尔科夫尼科夫加成产物。有趣的是，这种均相催化剂可以重复使用三遍，而不会显着降低活性。
• General and selective reductive amination of carbonyl compounds using a core–shell structured Co₃O₄/NGr@C catalyst
  作者：Tobias Stemmler、Felix A. Westerhaus、Annette-Enrica Surkus、Marga-Martina Pohl、Kathrin Junge、Matthias Beller

  DOI：10.1039/c4gc00536h

  日期：——

  The application of heterogenized non-noble metal-based catalysts in selective catalytic hydrogenation processes is still challenging. In this respect, the preparation of a well-defined cobalt-based catalyst was investigated by immobilization of the corresponding cobalt(II)-phenanthroline-chelate on Vulcan XC72R carbon powder. The formed core–shell structured cobalt/cobalt oxide nanocomposites are encapsulated by nitrogen-enriched graphene layers. This promising cheap heterogeneous catalyst allows for an efficient domino reductive amination of carbonyl compounds with nitroarenes.

  非贵金属基异质催化剂在选择性催化氢化过程中的应用仍然面临挑战。在此方面，通过将相应的二价钴-菲咯啉螯合物固定在Vulcan XC72R碳粉上，研究了制备结构明确的钴基催化剂。形成的核壳结构的钴/钴氧化物纳米复合物被富含氮的石墨烯层包裹。这种经济实惠的非均相催化剂能够实现羰基化合物与硝基芳烃的高效多米诺还原胺化反应。
• Visible-Light-Induced Copper-Catalyzed Intermolecular Markovnikov Hydroamination of Alkenes
  作者：Yang Xiong、Guozhu Zhang

  DOI：10.1021/acs.orglett.9b02863

  日期：2019.10.4

  A visible-light-induced copper-catalyzed intermolecular hydroamination of alkenes using commercially accessible primary and secondary amines has been established. This effective method exhibits good tolerance of a broad range of functional groups and provides a facile access to an array of valuable amines with Markovnikov regioselectivity. The process can be positively expected to be used in bioactive

  已经建立了使用可商购的伯胺和仲胺的可见光诱导的铜催化的烯烃的分子间加氢胺化。这种有效的方法表现出对各种官能团的良好耐受性，并提供了以马尔可夫尼科夫区域选择性轻松接触一系列有价值的胺的方法。可以肯定地预期该方法将用于生物活性胺中，并且可能在发现铜催化的加氢官能​​化反应中提供新的潜力。
• Synthesis of Group 4 Metal Complexes Stabilized by an Amine-Bridged Bis(phenolato) Ligand and Their Catalytic Behavior in Intermolecular Hydroamination Reactions
  作者：Qiu Sun、Yaorong Wang、Dan Yuan、Yingming Yao、Qi Shen

  DOI：10.1021/om401158a

  日期：2014.2.24

  bis(phenolato) ligand, have been synthesized and characterized. Although 1 and 2 were inactive in catalyzing intermolecular hydroamination reactions, cationic complexes generated in situ from treatment of 1 and 2 with borate [Ph3C][B(C6F5)4], respectively, were found to be highly active. In general, excellent yields (up to >99%) and 100% regioselectivity for a broad range of terminal alkynes and anilines

  锆和钛配合物1和2，带有胺桥连双（苯酚）配体，已经合成和表征。虽然1和2无活性在催化分子间加氢胺化反应，从治疗的原位产生的阳离子络合物1和2与硼酸[PH 3 C] [B（C 6 ˚F 5）4]分别被认为是高度活性的。一般情况下，优异的产率（高达> 99％）和为广泛末端炔烃和苯胺的100％的区域选择性分别为1个小时的反应时间内观察到。反应中度空间相互作用也导致了良好的收益率和适度的区域选择性的内部炔烃。动力学研究还进行，其提供了一些见解加氢胺化反应的机制。