potassium 3-chloro-4-methoxyphenyl trifluoroborate

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: potassium 3-chloro-4-methoxyphenyl trifluoroborate
• 英文别名: potassium (3-chloro-4-methoxyphenyl)trifluoroborate salt；Potassium (3-chloro-4-methoxyphenyl)trifluoroboranuide；potassium;(3-chloro-4-methoxyphenyl)-trifluoroboranuide
• 化学式: C₇H₆BClF₃O*K
• 分子量: 248.482
• InChiKey: HMWKVNLPNWUHPO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.59
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  potassium 3-chloro-4-methoxyphenyl trifluoroborate 在 lithium hydroxide monohydrate 、 silver trifluoromethanesulfonate 、 Selectfluor 作用下， 以 乙酸乙酯 为溶剂， 以77%的产率得到2-氯-4-氟苯甲醚
  参考文献：
  名称：

  Silver-mediated fluorination of potassium aryltrifluoroborates with Selectfluor®

  摘要：

  A simple and practical procedure for the silver-mediated fluorination of aryl- and heteroaryltrifluoroborates with electrophilic fluorine from Selectfluor (R) and LiOH center dot H2O is presented. The reaction procedure is simple and easy to set up, the process produces fluorinated arenes and heteroarenes in good to excellent yields and a wide range of electronically and structurally diverse substrates are tolerated. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.10.055
• 作为产物：
  描述：

  potassium fluoride 、 3-氯-4-甲氧基苯硼酸 在 酒石酸 作用下， 以 水 、 乙腈 、 四氢呋喃 为溶剂， 以90%的产率得到potassium 3-chloro-4-methoxyphenyl trifluoroborate
  参考文献：
  名称：

  精制硼-碘交换以获得多功能芳基化试剂

  摘要：

  芳基（中）碘鎓盐是多面芳基转移试剂，通过硼-碘交换合成。与以前的条件相比，对亲核（芳基硼）和亲电子（异丙叉基-λ 3 -碘）反应组分的改性可提高产率并加快反应时间。机理研究揭示了一种更像金属转移而不是 S E Ar 的途径。

  DOI：

  10.1039/d1cc06341c

文献信息

• Electrochemical <i>ipso</i> ‐Thiocyanation of Arylboron Compounds
  作者：Marco Dyga、Davit Hayrapetyan、Raja K. Rit、Lukas J. Gooßen

  DOI：10.1002/adsc.201900156

  日期：2019.8.5

  An operationally simple electrochemical method for the transition‐metal‐free ipso‐thiocyanation of arylboronic acids and aryl trifluoroborates has been developed. The SCN electrophile is generated in situ by anodic oxidation of thiocyanate anions, which avoids formation of salt waste and prevents unwanted side reactions arising from chemical oxidants. The reaction proceeds regiospecifically, and the

  对于过渡金属不含操作简单电化学方法本位-thiocyanation的芳基硼酸和芳基三氟硼酸已经研制成功。SCN亲电试剂是通过硫氰酸根阴离子的阳极氧化原位产生的，避免了盐分的形成并防止了由化学氧化剂引起的不良副反应。反应以区域特异性方式进行，范围扩展至未活化的芳族体系。
• Copper-Mediated Oxidative Trifluoromethylthiolation of Potassium Aryltrifluoroborates with Elemental Sulfur and Ruppert–Prakash Reagent
  作者：Srinivas Dubbaka、Azmi Atthunuri、Koraboina Prakash、Prabhu Rangabashyam、Satyanarayana Gadde、Rajesh Kothandaraman

  DOI：10.1055/s-0035-1561565

  日期：——

  procedure for the copper-mediated oxidative trifluoromethylthiolation of potassium aryl- and heteroaryltrifluoroborates with Ruppert–Prakash reagent and elemental sulfur is presented. Aryl trifluoromethyl thioethers can be prepared in good to moderate yield under mild reaction conditions. A facile procedure for the copper-mediated oxidative trifluoromethylthiolation of potassium aryl- and heteroaryltrifluoroborates

  §这些作者同等贡献这项工作。 抽象的 提出了使用Ruppert-Prakash试剂和元素硫对铜介导的芳基和杂芳基三氟硼酸钾的氧化三氟甲基硫醇化的简便方法。芳基三氟甲基硫醚可以在温和的反应条件下以良好至中等的产率制备。 提出了使用Ruppert-Prakash试剂和元素硫对铜介导的芳基和杂芳基三氟硼酸钾的氧化三氟甲基硫醇化的简便方法。芳基三氟甲基硫醚可以在温和的反应条件下以良好至中等的产率制备。
• Oxidative Cycloaddition Reactions of Arylboron Reagents via a One-pot Formal Dehydroboration Sequence
  作者：Shubhendu S. Karandikar、Bryan E. Metze、Riley A. Roberts、David R. Stuart

  DOI：10.1021/acs.orglett.3c02379

  日期：2023.9.1

  are widely available and synthetically useful reagents in which the boron group is typically substituted. Herein, we show that the boron group and ortho-hydrogen atom are substituted in a formal cycloaddition reaction. This transformation is enabled by a one-pot sequence involving diaryliodonium and aryne intermediates. The scope of arylboron reagents and arynophiles is demonstrated, and the method

  芳基硼化合物是广泛可用且合成上有用的试剂，其中硼基团通常被取代。在此，我们证明硼基团和邻氢原子在正式的环加成反应中被取代。这种转化是通过涉及二芳基碘鎓和芳炔中间体的一锅法序列实现的。论证了芳基硼试剂和亲亲试剂的范围，并将该方法应用于研究候选药物的正式合成。
• Silver-mediated fluorination of potassium aryltrifluoroborates with Selectfluor®
  作者：Srinivas Reddy Dubbaka、Venkateswara Reddy Narreddula、Satyanarayana Gadde、Thresen Mathew

  DOI：10.1016/j.tet.2014.10.055

  日期：2014.12

  A simple and practical procedure for the silver-mediated fluorination of aryl- and heteroaryltrifluoroborates with electrophilic fluorine from Selectfluor (R) and LiOH center dot H2O is presented. The reaction procedure is simple and easy to set up, the process produces fluorinated arenes and heteroarenes in good to excellent yields and a wide range of electronically and structurally diverse substrates are tolerated. (C) 2014 Elsevier Ltd. All rights reserved.
• Refining boron–iodane exchange to access versatile arylation reagents
  作者：Shubhendu S. Karandikar、David R. Stuart

  DOI：10.1039/d1cc06341c

  日期：——

  Aryl(Mes)iodonium salts, which are multifaceted aryl transfer reagents, are synthesized via boron-iodane exchange. Modification to both the nucleophilic (aryl boron) and electrophilic (mesityl–λ3–iodane) reaction components results in improved yield and faster reaction time compared to previous conditions. Mechanistic studies reveal a pathway that is more like transmetallation than SEAr.

  芳基（中）碘鎓盐是多面芳基转移试剂，通过硼-碘交换合成。与以前的条件相比，对亲核（芳基硼）和亲电子（异丙叉基-λ 3 -碘）反应组分的改性可提高产率并加快反应时间。机理研究揭示了一种更像金属转移而不是 S E Ar 的途径。