2-(2-Methylphenyl)-4-(trifluoromethyl)pyridine | 1186689-46-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 2-(2-Methylphenyl)-4-(trifluoromethyl)pyridine
• CAS: 1186689-46-2
• 化学式: C₁₃H₁₀F₃N
• 分子量: 237.224
• InChiKey: IVDJKYJZANAEDJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(2-Methylphenyl)-4-(trifluoromethyl)pyridine 在 N-氯代丁二酰亚胺 、 palladium diacetate 、 溶剂黄146 作用下， 反应 12.0h， 生成
  参考文献：
  名称：

  Mechanistic Comparison between Pd-Catalyzed Ligand-Directed C−H Chlorination and C−H Acetoxylation

  摘要：

  This communication describes detailed investigations of the mechanism of the Pd-catalyzed C-H chlorination and acetoxylation of 2-o-tolylpyridine. Under the conditions examined, both reactions proceed via rate-limiting cyclopalladation. However, substrate and catalyst order as well as Hammett data Indicate that the intimate mechanism of cyclopalladation differs significantly between PdCl2-catalyzed chlorination and Pd(OAc)(2)-catalyzed acetoxylation.

  DOI：

  10.1021/ol901820w

文献信息

• Room-Temperature C–H Arylation: Merger of Pd-Catalyzed C–H Functionalization and Visible-Light Photocatalysis
  作者：Dipannita Kalyani、Kate B. McMurtrey、Sharon R. Neufeldt、Melanie S. Sanford

  DOI：10.1021/ja208068w

  日期：2011.11.23

  This communication describes the development of a room-temperature ligand-directed C-H arylation reaction using aryldiazonium salts. This was achieved by the successful merger of palladium-catalyzed C-H functionalization and visible-light photoredox catalysis. The new method is general for a variety of directing groups and tolerates many common functional groups.

  该通讯描述了使用芳基重氮盐进行室温配体导向的 CH 芳基化反应的开发。这是通过钯催化的 CH 官能化和可见光光氧化还原催化的成功合并实现的。新方法适用于各种导向基团，并能容忍许多常见的官能团。
• Aromatic and olefinic C-H alkenylation by catalysis with spirocyclic NHC Ru(IV) pincer complex
  作者：Heng Cai、Yong-Qiang Tu、Ka Lu、Qi-Long Chen、Fu-Min Zhang、Xiao-Ming Zhang、Yuan-Jiang Pan、Zhi-Bo Yan

  DOI：10.1007/s11426-022-1541-5

  日期：2023.10

  Catalyst innovation lies at the heart of transition-metal-catalyzed reaction development. In this article, we have explored the C(sp2)—H alkenylation activity with novel spirocyclic N-heterocyclic carbene (NHC)-based cyclometalated ruthenium pincer catalyst system, SNRu-X. After screening catalyst and condition, a high valent Ru(IV) dioxide (X = O2) species has demonstrated superior reactivity in the

  催化剂创新是过渡金属催化反应开发的核心。在本文中，我们探索了 C(sp 2 )-H 烯基化活性与新型螺环 N-杂环卡宾 (NHC) 基环金属化钌钳形催化剂体系SNRu-X。经过筛选催化剂和条件后，高价 Ru(IV) 二氧化（X = O 2) 物种在芳香族和烯烃 CH 键与未活化的烯基溴化物和三氟甲磺酸酯的催化烯基化反应中表现出优异的反应性。该反应实现了多种（杂）芳族烯烃和二烯的简单构建，具有良好的收率和独特的选择性。初步的机理研究表明，该反应可能通过单电子转移 (SET) 触发的氧化加成进行，从而为依赖于活化烯基前体的经典烯基化反应提供有价值的补充。