| 1346233-06-4

• 分子结构分类: 有机化合物 - 有机氮化合物
• CAS: 1346233-06-4
• 化学式: C₁₅H₂₄FN₃
• 分子量: 265.374
• InChiKey: QHALASCPLKEODX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.73
• 重原子数：
  19.0
• 可旋转键数：
  0.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  27.3
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  四(乙腈)三氟甲磺酸铜(I) 、 、 四丁基氯化铵 以 丙酮 为溶剂， 生成
  参考文献：
  名称：

  Nucleophilic Aryl Fluorination and Aryl Halide Exchange Mediated by a Cu^I/Cu^III Catalytic Cycle

  摘要：

  Copper-catalyzed halide exchange reactions under very mild reaction conditions are described for the first time using a family of model aryl halide substrates. All combinations of halide exchange (I, Br, Cl, F) are observed using catalytic amounts of Cu-I. Strikingly, quantitative fluorination of aryl X substrates is also achieved catalytically at room temperature, using common F- sources, via the intermediacy of aryl-Cu-III-X species. Experimental and computational data support a redox Cu-I/Cu-III catalytic cycle involving aryl X oxidative addition at the Cu-I center, followed by halide exchange and reductive elimination steps. Additionally, defluorination of the aryl-F model system can be also achieved with Cu-I at room temperature operating under a Cu-I/Cu-III redox pair.

  DOI：

  10.1021/ja2058567
• 作为产物：
  描述：

  2,6-二甲基氟苯 在 N-溴代丁二酰亚胺(NBS) 、 氢溴酸 、 caesium carbonate 、 溶剂黄146 、 苯酚 、 过氧化苯甲酰 作用下， 以 氯仿 、 乙腈 为溶剂， 反应 84.0h， 生成
  参考文献：
  名称：

  Nucleophilic Aryl Fluorination and Aryl Halide Exchange Mediated by a Cu^I/Cu^III Catalytic Cycle

  摘要：

  Copper-catalyzed halide exchange reactions under very mild reaction conditions are described for the first time using a family of model aryl halide substrates. All combinations of halide exchange (I, Br, Cl, F) are observed using catalytic amounts of Cu-I. Strikingly, quantitative fluorination of aryl X substrates is also achieved catalytically at room temperature, using common F- sources, via the intermediacy of aryl-Cu-III-X species. Experimental and computational data support a redox Cu-I/Cu-III catalytic cycle involving aryl X oxidative addition at the Cu-I center, followed by halide exchange and reductive elimination steps. Additionally, defluorination of the aryl-F model system can be also achieved with Cu-I at room temperature operating under a Cu-I/Cu-III redox pair.

  DOI：

  10.1021/ja2058567

文献信息

• Oxidant-Free Au(I)-Catalyzed Halide Exchange and C_sp2–O Bond Forming Reactions
  作者：Jordi Serra、Christopher J. Whiteoak、Ferran Acuña-Parés、Marc Font、Josep M. Luis、Julio Lloret-Fillol、Xavi Ribas

  DOI：10.1021/jacs.5b08756

  日期：2015.10.21

  character, Au(I)/Au(III) redox properties or a combination of both. As a result of the high oxidation potential of the Au(I)/Au(III) couple, redox catalysis involving Au typically requires the use of a strong external oxidant. This study demonstrates unusual external oxidant-free Au(I)-catalyzed halide exchange (including fluorination) and Csp2-O bond formation reactions utilizing a model aryl halide macrocyclic

  Au 已被证明通过利用其 π 路易斯酸特性、Au(I)/Au(III) 氧化还原特性或两者的组合来介导许多有机转化。由于 Au(I)/Au(III) 对的高氧化电位，涉及 Au 的氧化还原催化通常需要使用强外部氧化剂。该研究展示了不寻常的无外部氧化剂 Au(I) 催化的卤化物交换（包括氟化）和使用模型芳基卤化物大环底物的 Csp2-O 键形成反应。此外，卤化物交换和 Csp2-O 偶联反应性也可以外推到带有单个螯合基团的底物，从而进一步了解反应机制。这项工作提供了无外部氧化剂的 Au(I) 催化碳-杂原子交叉偶联反应的第一个例子。