8-(trifluoromethyl)quinolin-4-yl trifluoromethanesulfonate | 1161941-00-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 8-(trifluoromethyl)quinolin-4-yl trifluoromethanesulfonate
• 英文别名: 8-(trifluoromethyl)quinolin-4-yl trifllate；[8-(Trifluoromethyl)quinolin-4-yl] trifluoromethanesulfonate；[8-(trifluoromethyl)quinolin-4-yl] trifluoromethanesulfonate
• CAS: 1161941-00-9
• 化学式: C₁₁H₅F₆NO₃S
• 分子量: 345.222
• InChiKey: OQXPRRGSSXYFJH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  64.6
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  8-(trifluoromethyl)quinolin-4-yl trifluoromethanesulfonate 在 乙酸酐 、 sodium iodide 作用下， 以 乙腈 为溶剂， 以97%的产率得到4-iodo-8-(trifluoromethyl)quinoline
  参考文献：
  名称：

  Microwave-Assisted Trans-Halogenation Reactions of Various Chloro-, Bromo-, Trifluoromethanesulfonyloxy- and Nonafluorobutanesulfonyloxy-Substituted Quinolines, Isoquinolines, and Pyridines Leading to the Corresponding Iodinated Heterocycles

  摘要：

  Microwave irradiation of certain chloro-, bromo-, trifluoromethanesulfonyloxy- and nonafluorobutanesulfonyloxy-substituted quinolines in the presence of acetic. anhydride and sodium iodide leads, via a trans-halogenation process, to the corresponding iodides in high yield. Related conversions involving pyridines and isoquinolines can also be achieved under similar conditions.

  DOI：

  10.1021/jo9008386
• 作为产物：
  描述：

  8-(三氟甲基)喹啉-4(1H)-酮 、 三氟甲磺酸酐 生成 8-(trifluoromethyl)quinolin-4-yl trifluoromethanesulfonate
  参考文献：
  名称：

  An Improved Catalyst System for the Pd-Catalyzed Fluorination of (Hetero)Aryl Triflates

  摘要：

  The stable Pd(0) species [(1,5-cyclooctadiene)(L.Pd)(2)] (L = AdBrettPhos) has been prepared and successfully evaluated as a precatalyst for the fluorination of aryl triflates derived from biologically active and heteroaryl phenols, challenging substrates for our previously reported catalyst system. Additionally, this precatalyst activates at room temperature under neutral conditions, generates 1,5-cyclooctadiene as the only byproduct, and leads to overall cleaner reaction profiles.

  DOI：

  10.1021/ol402859k

文献信息

• The Quest for the Ideal Base: Rational Design of a Nickel Precatalyst Enables Mild, Homogeneous C–N Cross-Coupling
  作者：Richard Y. Liu、Joseph M. Dennis、Stephen L. Buchwald

  DOI：10.1021/jacs.0c00286

  日期：2020.3.4

  Palladium-catalyzed amination reactions using soluble organic bases have provided a solution to the many issues associated with heterogeneous reaction conditions. Still, homogeneous C-N cross-coupling approaches cannot yet employ bases as weak and economical as trialkylamines. Furthermore, organic base-mediated methods have not been developed for Ni(0/II) catalysis, despite some advantages of such systems

  使用可溶性有机碱的钯催化胺化反应为与多相反应条件相关的许多问题提供了解决方案。尽管如此，均相 CN 交叉偶联方法尚不能使用与三烷基胺一样弱且经济的碱。此外，尽管有机碱介导的方法与类似的 Pd 基催化剂相比具有一些优势，但尚未开发出用于 Ni(0/II) 催化的有机碱介导方法。我们设计了一种新的空气稳定且易于制备的 Ni(II) 预催化剂，其带有缺电子的双齿膦配体，能够使用三乙胺 (TEA) 作为碱使芳基三氟甲磺酸酯与芳基胺交叉偶联。该方法可以容忍空间拥挤的偶联伙伴，以及带有碱和亲核试剂敏感官能团的偶联伙伴。借助密度泛函理论 (DFT) 计算，我们确定缺电子辅助配体降低了 Ni 键合胺的 pKa 和从所得 Ni(II)-酰胺络合物还原消除的障碍。此外，我们确定，由于空间因素，排除 Ni 催化剂和碱之间的路易斯酸碱络合对于避免催化剂抑制很重要。