3-fluoro-N-(quinolin-8-yl)-[1,1'-biphenyl]-2-carboxamide

• 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: 3-fluoro-N-(quinolin-8-yl)-[1,1'-biphenyl]-2-carboxamide
• 英文别名: 2-fluoro-6-phenyl-N-quinolin-8-ylbenzamide
• 化学式: C₂₂H₁₅FN₂O
• 分子量: 342.372
• InChiKey: WOOIYUDZMNLIAK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  42
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  邻氟苯甲酸 在 potassium fluoride 、 氯化亚砜 、 palladium diacetate 、 特戊酸钠 、 三乙胺 、 对苯醌 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 4.0h， 生成 3-fluoro-N-(quinolin-8-yl)-[1,1'-biphenyl]-2-carboxamide
  参考文献：
  名称：

  通过定向 C-H 活化进行 Aryne 多组分反应

  摘要：

  许多研究人员最近探索了在导向基团的帮助下通过邻位 CH 活化的芳基化。在此，开发了一种使用 8-氨基喹啉作为双齿导向基团的钯催化的 C-H 芳基化反应。该反应仅提供 CH 芳基化，与观察到相应异喹诺酮环化的先前方法不同。更有趣的是，当加入丙烯酸甲酯和丙烯腈时，观察到连续的 CH 官能化；这导致与芳基的 CH 烯化，芳基由芳烃前体安装。

  DOI：

  10.1002/chem.202100205

文献信息

• Cobalt‐Catalyzed Hiyama‐type C‐H Activation with Arylsiloxanes: Versatile Access to Highly‐Ortho‐Decorated Biaryls
  作者：Qingqing Bu、Elżbieta Gońka、Krzysztof Kuciński、Lutz Ackermann

  DOI：10.1002/chem.201806114

  日期：——

  Versatile direct Hiyama‐type C−H arylations of benzamides were accomplished with organosiloxanes by chelation‐assisted cobalt catalysis. The C−H arylation featured broad substrate scope, including challenging C(sp3)−H activation, the use of γ‐valerolactone as biomass‐derived solvent, and selectively provided the desired biaryls, even when being highly sterically hindered.

  苯甲酰胺的多功能直接Hiyama型CH芳基化反应是通过有机硅氧烷通过螯合辅助钴催化实现的。C-H芳基化具有广泛的底物范围，包括具有挑战性的C（sp 3）-H活化，使用γ-戊内酯作为生物质衍生的溶剂，并选择性地提供了所需的联芳基，即使在空间高度受阻的情况下也是如此。
• Nickel(II)-Catalyzed Direct Arylation of C–H Bonds in Aromatic Amides Containing an 8-Aminoquinoline Moiety as a Directing Group
  作者：Ayana Yokota、Yoshinori Aihara、Naoto Chatani

  DOI：10.1021/jo501697n

  日期：2014.12.19

  Arylation via the cleavage of the ortho CH bonds by a nickel-catalyzed reaction of aromatic amides containing an 8-aminoquinoline moiety with aryl iodides is reported. The reaction shows a high functional group compatibility. The reaction proceeds in a highly selective manner at the less hindered CH bonds in the reaction of meta-substituted aromatic amides, irrespective of the electronic nature of the substituents. Electron-withdrawing groups on the aromatic amides facilitate the reaction. Various mechanistic experiments, such as deuterium labeling experiments, Hammett studies, competition experiments, and radical trap experiments, have been made for better understanding the reaction mechanism. It is found that the cleavage of CH bonds is reversible on the basis of the deuterium labeling experiments. Both Ni(II) and Ni(0) show a high catalytic activity, but the results of mechanistic experiments suggest that a Ni(0)/Ni(II) catalytic cycle is not involved.
• Aryne Multicomponent Reactions by Directed C−H Activation
  作者：Sunil Kumar Sunnam、Jitendra D. Belani

  DOI：10.1002/chem.202100205

  日期：2021.6.16

  Arylation via ortho C−H activation by the aid of directing groups has been explored recently by many researchers. Herein, a palladium-catalyzed C−H arylation using 8-aminoquinoline as a bidentate directing group has been developed. The reaction furnishes only C−H arylation, unlike previous methods where cyclization to corresponding isoquinolones is observed. More interestingly, sequential C−H functionalization

  许多研究人员最近探索了在导向基团的帮助下通过邻位 CH 活化的芳基化。在此，开发了一种使用 8-氨基喹啉作为双齿导向基团的钯催化的 C-H 芳基化反应。该反应仅提供 CH 芳基化，与观察到相应异喹诺酮环化的先前方法不同。更有趣的是，当加入丙烯酸甲酯和丙烯腈时，观察到连续的 CH 官能化；这导致与芳基的 CH 烯化，芳基由芳烃前体安装。