2-D-1,3,5-trifluorobenzene | 767-78-2

• 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: 2-D-1,3,5-trifluorobenzene
• 英文别名: 1,3,5-Trifluor-benzol-d1；1-deutero-2,4,6-trifluorobenzene；2-deuterio-1,3,5-trifluoro-benzene；2-Deuterio-1,3,5-trifluorobenzene；2-deuterio-1,3,5-trifluorobenzene
• CAS: 767-78-2
• 化学式: C₆H₃F₃
• 分子量: 133.077
• InChiKey: JXUKFFRPLNTYIV-MICDWDOJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2,4,6-三氟苯硼酸 在 potassium hydroxide 作用下， 以 重水 为溶剂， 生成 2-D-1,3,5-trifluorobenzene
  参考文献：
  名称：

  Base-Promoted Protodeboronation of 2,6-Disubstituted Arylboronic Acids

  摘要：

  Facile based promoted deboronation of electron-deficient arylboronate esters was observed for arylboronates containing two ortho electron-withdrawing group (EWG) substituents. Among 30 representative boronates, only the diortho-substituted species underwent facile C-B fission in aqueous basic conditions (200 mM hydroxide). These results provide fundamental insight into deboronative mechanisms with implications for cross-coupling reactions, regioselective deuteration/tritiation for isotopic labeling, and the design of new F-18-trifluoroborate radioprosthetics.

  DOI：

  10.1021/jo500734z

文献信息

• Metal-Free sp²-C–H Borylation as a Common Reactivity Pattern of Frustrated 2-Aminophenylboranes
  作者：Konstantin Chernichenko、Markus Lindqvist、Bianka Kótai、Martin Nieger、Kristina Sorochkina、Imre Pápai、Timo Repo

  DOI：10.1021/jacs.6b00819

  日期：2016.4.13

  olefinic C-H bonds with 2-aminophenylboranes. Computational and experimental studies reveal that the metal-free C-H insertion proceeds via a frustrated Lewis pair mechanism involving heterolytic splitting of the C-H bond by cooperative action of the amine and boryl groups. The adapted geometry of the reactive B and N centers results in an unprecedentently low kinetic barrier for both insertion into the

  CH 硼酸化是一种强大且原子效率高的方法，可将廉价且丰富的化学品转化为用于生产精细化学品和功能材料的多功能有机试剂。在此，我们报告了芳香族和烯烃 CH 键与 2-氨基苯基硼烷的简便 CH 硼酸化。计算和实验研究表明，不含金属的 CH 插入是通过受挫的路易斯对机制进行的，该机制涉及通过胺和硼基团的协同作用使 CH 键异裂。反应性 B 和 N 中心的适应性几何结构导致了前所未有的低动力学障碍，用于插入 sp(2)-CH 键和 sp(2)-CB 键在 2-氨基苯基(芳基)中的分子内质子化-或-（烯基）硼酸盐。这种常见的反应模式可作为各种催化反应的平台，例如 CH 硼化和炔烃的氢化。特别是，我们证明了简单的 2-氨基吡啶鎓盐可以有效地催化环戊二烯与儿茶酚硼烷的 CH 硼化。该反应可能是由与 2-氨基苯基硼烷等电子的硼物种介导的。
• Deuterium Exchange between Arenes and Deuterated Solvents in the Absence of a Transition Metal: Synthesis of D-Labeled Fluoroarenes
  作者：Vanesa Salamanca、Ana C. Albéniz

  DOI：10.1002/ejoc.202000284

  日期：2020.6.16

  Easy deuteration of fluoroarenes with good selectivity can be achieved by H/D exchange with inexpensive deuterated solvents in a sustainable way. Just alkali metal bases are enough to bring about the exchange, which does not require a transition metal. This exchange should be taken into account when using deuterium labeling for mechanistic studies under close related conditions.

  通过与廉价的氘代溶剂以可持续的方式进行H / D交换，可以轻松实现具有良好选择性的氟代芳烃的氘代。仅仅碱金属碱就足以引起交换，这不需要过渡金属。使用氘标记进行密切相关条件下的机理研究时，应考虑这种交换。
• Ag(I)-Catalyzed C–H Activation: The Role of the Ag(I) Salt in Pd/Ag-Mediated C–H Arylation of Electron-Deficient Arenes
  作者：Daniel Whitaker、Jordi Burés、Igor Larrosa

  DOI：10.1021/jacs.6b04726

  日期：2016.7.13

  The use of stoichiometric Ag(I)-salts as additives in Pd-catalyzed C-H functionalization reactions is widespread. It is commonly proposed that this additive acts as an oxidant or as a halide scavenger promoting Pd-catalyst turnover. We demonstrate that, contrary to current proposals, phosphine ligated Ag(I)-carboxylates can efficiently carry out C-H activation on electron-deficient arenes. We show

  在 Pd 催化的 CH 官能化反应中广泛使用化学计量的 Ag(I)-盐作为添加剂。通常认为这种添加剂可作为氧化剂或卤化物清除剂，促进 Pd 催化剂的转化。我们证明，与目前的提议相反，膦连接的 Ag(I)-羧酸盐可以有效地对缺电子芳烃进行 CH 活化。我们通过化学计量和动力学研究的组合表明，(PPh3)Ag-羧酸盐负责 Pd 催化的 Cr(CO)3 络合氟苯芳基化反应中的 CH 活化步骤。此外，反应速率受 Ag(I)-CH 活化速率的控制，导致 Pd 催化剂的数量级为零。
• ——
  作者：H.-J. Frohn、N. Y. Adonin、V. V. Bardin、V. F. Starichenko

  DOI：10.1002/1521-3749(200213)628:13<2834::aid-zaac2834>3.0.co;2-2

  日期：——

  Polyfluorinated phenyl(dihydroxy)boranes C6H5-nFnB(OH)(2) (n = 3 - 5) underwent hydrodeboration (formal replacement of the (dihydroxy)boryl group by hydrogen) in the presence of bases (MeOH, 33% H2O-MeOH, KOH (1 equiv.)/33% H2O-MeOH, pyridine and 9% D2O-pyridine) and formed the fluoroaromatic compounds ArH or ArD, respectively. The rate of reaction depends on the number of fluorine atoms in the phenyl group and on the position of the fluorine atoms, relative to the B(OH)(2) substituent.
• Base-Promoted Protodeboronation of 2,6-Disubstituted Arylboronic Acids
  作者：Jerome Lozada、Zhibo Liu、David M. Perrin

  DOI：10.1021/jo500734z

  日期：2014.6.6

  Facile based promoted deboronation of electron-deficient arylboronate esters was observed for arylboronates containing two ortho electron-withdrawing group (EWG) substituents. Among 30 representative boronates, only the diortho-substituted species underwent facile C-B fission in aqueous basic conditions (200 mM hydroxide). These results provide fundamental insight into deboronative mechanisms with implications for cross-coupling reactions, regioselective deuteration/tritiation for isotopic labeling, and the design of new F-18-trifluoroborate radioprosthetics.