对乙基苯基三氟硼酸钾 | 1160725-33-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 对乙基苯基三氟硼酸钾
• 英文名称: potassium p-ethylphenyltrifluoroborate
• 英文别名: Potassium (4-ethylphenyl)trifluoroboranuide；potassium;(4-ethylphenyl)-trifluoroboranuide
• CAS: 1160725-33-6
• 化学式: C₈H₉BF₃*K
• 分子量: 212.064
• InChiKey: KFIINFZVJLVXSQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.69
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 储存条件：
  存储条件：2-8℃，密封保存，并保持干燥。

反应信息

• 作为反应物：
  描述：

  对乙基苯基三氟硼酸钾 在 4-二甲氨基吡啶 、 水 、 copper(II) acetate monohydrate 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以25%的产率得到4,4'-oxybis(ethylbenzene)
  参考文献：
  名称：

  Copper(II)-Mediated O-Arylation of Protected Serines and Threonines

  摘要：

  An effective protocol toward the O-arylation of β-hydroxy-α-amino acid substrates serine and threonine has been developed via Chan-Lam cross-coupling. This Cu(II)-catalyzed transformation involves benign open-flask conditions that are well-tolerated with a variety of protected (Boc-, Cbz-, Tr-, and Fmoc-) serine and threonine derivatives and various potassium organotrifluoroborates and boronic acids.

  DOI：

  10.1021/ol5024689

文献信息

• Pd-catalyzed cross-coupling reactions of arenediazonium salts with arylsilanes and aryltrifluoroborates in water
  作者：Kai Cheng、Baoli Zhao、Sai Hu、Xian-Man Zhang、Chenze Qi

  DOI：10.1016/j.tetlet.2013.09.001

  日期：2013.11

  Pd-catalyzed cross-coupling reactions of various arenediazonium salts with ArSi(OR)3 and KArBF3 have been achieved in good to excellent yields under simple aerobic conditions in water at room temperature. The functional group tolerance makes these transformations as attractive alternatives to the traditional cross-coupling approaches. Furthermore, the sequence can also be performed in a one-pot domino

  在简单的好氧条件下，在室温下于水中将各种芳族重氮鎓盐与ArSi（OR）3和KArBF 3进行Pd催化的交叉偶联反应，得到的产率高至优。官能团的耐受性使这些转化成为传统交叉偶联方法的诱人替代品。此外，该序列也可以在一锅多米诺骨牌过程中进行，省去了中间芳烃重氮盐的分离。
• A Zwitterionic Palladium(II) Complex as a Precatalyst for Neat-Water-Mediated Cross-Coupling Reactions of Heteroaryl, Benzyl, and Aryl Acid Chlorides with Organoboron Reagents
  作者：Visannagari Ramakrishna、Morla Jhansi Rani、Nareddula Dastagiri Reddy

  DOI：10.1002/ejoc.201701241

  日期：2017.12.29

  A zwitterionic palladium(II) complex has been found to be an efficient catalyst for Suzuki–Miyaura cross‐coupling reactions of aryl and heteroaryl organoboron reagents with various heteroaryl chlorides, aryl‐ and heteroarylmethyl chlorides, and aryl acid chlorides in neat water.

  两性离子钯（II）络合物是在纯净水中使芳基和杂芳基有机硼试剂与各种杂芳基氯化物，芳基和杂芳基甲基氯化物以及芳基酰氯发生铃木–宫浦交叉偶联反应的有效催化剂。
• One-Pot Method for Regioselective Bromin­ation and Sequential Carbon-Carbon Bond-Forming Reactions of Allylic Alcohol Derivatives
  作者：Noriki Kutsumura、Yusuke Matsubara、Kentaro Niwa、Ai Ito、Takao Saito

  DOI：10.1002/ejoc.201300173

  日期：2013.6

  An efficient one-pot method for the regioselective bromination of allylic alcohol derivatives (two-step reaction sequence) followed by Sonogashira, Negishi, or Suzuki–Miyaura coupling reactions in the same reaction vessel (three-step reaction sequence) has been developed. The key reaction in these one-pot systems is the regioselective DBU-promoted trans HBr elimination of vicinal dibromides bearing

  已经开发了一种有效的一锅法，用于烯丙醇衍生物的区域选择性溴化（两步反应顺序），然​​后在同一反应容器中进行 Sonogashira、Negishi 或 Suzuki-Miyaura 偶联反应（三步反应顺序）。这些一锅系统中的关键反应是区域选择性 DBU 促进的反式 HBr 消除带有相邻 O 官能团的邻位二溴化物。
• Weak, bidentate chelating group assisted cross-coupling of C(sp³)–H bonds in aliphatic acid derivatives with aryltrifluoroborates
  作者：Zhihua Cai、Shangda Li、Yuzhen Gao、Lei Fu、Gang Li

  DOI：10.1039/c8cc07481j

  日期：——

  A protocol of Pd(II)-catalyzed, weak bidentate directing group assisted β-C(sp3)–H activation/cross-coupling with organoboron reagents has been achieved, affording arylation of aliphatic acid derivatives that contain α-hydrogen atoms in moderate to good yields. The potential of this method for an asymmetric β-C(sp3)–H arylation via desymmetrization was also presented.

  已实现了由Pd（II）催化的弱双齿指导基团辅助的β-C（sp 3）-H活化/与有机硼试剂交叉偶联的方案，使含α-氢原子的脂肪族酸衍生物芳构化高产。还介绍了该方法通过去对称化进行不对称β-C（sp 3）-H芳构化的潜力。
• Nickel/TiO2-catalyzed Suzuki–Miyaura cross-coupling of arylboronic acids with aryl halides in MeOH/H2O
  作者：Mona Hosseini-Sarvari、Abdulhamid Dehghani

  DOI：10.1007/s00706-023-03052-9

  日期：2023.4

  The catalyst structure was investigated by XRD, SEM, FT–IR, and N2 adsorption–desorption isotherm analysis and then successfully applied for the synthesis of biaryl compounds through a Suzuki–Miyaura cross-coupling reaction. A wide variety of biaryl compounds were successfully synthesized through the developed catalytic process in MeOH/H2O, and all desired biaryl compounds were obtained in good to

  Ni/TiO 2纳米粒子被合成为可分离和可重复使用的纳米催化剂。通过 XRD、SEM、FT-IR 和 N 2吸附-脱附等温线分析研究了催化剂结构，然后通过 Suzuki-Miyaura 交叉偶联反应成功应用于联芳基化合物的合成。通过在 MeOH/H 2 O 中开发的催化工艺成功合成了多种联芳基化合物，并且在相对较短的反应时间后，所有所需的联芳基化合物都以良好到极好的产率 (60–100%) 获得。幸运的是，催化剂可以很容易地回收并重复使用至少五次，而不会对产品的收率产生任何重大影响。 图形概要