2,3-二甲基苯基三氟硼酸钾 | 1412414-17-5

• 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: 2,3-二甲基苯基三氟硼酸钾
• 英文名称: potassium (2,3-dimethylphenyl)trifluoroborate
• 英文别名: Potassium 2,3-dimethylphenyltrifluoroborate；potassium;(2,3-dimethylphenyl)-trifluoroboranuide
• CAS: 1412414-17-5
• 化学式: C₈H₉BF₃*K
• 分子量: 212.064
• InChiKey: BYBSQSLXIANVCV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.64
• 重原子数：
  13
• 可旋转键数：
  0
• 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

反应信息

• 作为反应物：
  描述：

  2,3-二甲基苯基三氟硼酸钾 在 lithium hydroxide monohydrate 、 silver trifluoromethanesulfonate 、 Selectfluor 作用下， 以 乙酸乙酯 为溶剂， 以90%的产率得到3-氟邻二甲苯
  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：

  2,3-二甲基苯硼酸 在 potassium hydrogen difluoride 作用下， 以 乙醚 、 水 为溶剂， 反应 3.0h， 以99%的产率得到2,3-二甲基苯基三氟硼酸钾
  参考文献：
  名称：

  杂芳基和芳基三氟硼酸酯的有机催化不对称共轭加成：Discoipyrrole D的合成策略。

  摘要：

  使用相应的三氟硼酸盐作为亲核试剂，通过有机催化对映选择性共轭加成反应形成双-杂芳基或双-芳基立体中心。对照研究表明，在无水条件下氟化物离解是必要的。该策略适用于盘状吡咯D的合成，盘状吡咯D是BR5成纤维细胞迁移的抑制剂。

  DOI：

  10.1002/anie.201503528

文献信息

• Axial Chirality about Boron–Carbon Bond: Atropisomeric Azaborines
  作者：Andrea Mazzanti、Elia Mercanti、Michele Mancinelli

  DOI：10.1021/acs.orglett.6b01159

  日期：2016.6.3

  The preparation of atropisomeric 2,1-borazaronaphthalenes is described. Resolution of the atropisomeric pair was achieved by preparative Chiral Stationary Phase HPLC (CSP-HPLC). The absolute configuration of the stereogenic axis was derived from Time-Dependent DFT (TD-DFT) simulation of the Electronic Circular Dichroism spectra (ECD). X-ray diffraction and Dynamic NMR data allowed structural and dynamic

  描述了阻转异构体2，1-硼硼烷萘的制备。阻转异构体对的拆分通过制备型手性固定相HPLC（CSP-HPLC）实现。立体轴的绝对配置是从电子圆二色性光谱（ECD）的时变DFT（TD-DFT）模拟得出的。X射线衍射和动态NMR数据可与类似的等构碳化合物进行结构和动态比较。
• (Ph3P)AuCl-catalyzed homocoupling of arylboronic acids under benchtop conditions: Synthesis of biphenyls
  作者：Silvia Roscales、Francisco Sánchez-Sancho、Aurelio G. Csáky

  DOI：10.1016/j.mcat.2023.113281

  日期：2023.8

  (Ph3P)AuCl was discovered to be a powerful catalyst in the homocoupling of arylboronic acids and potassium aryltrifluoroborates for the synthesis of symmetrical biaryls. The reactions take place under benchtop reaction conditions in 96% EtOH at temperatures between rt and 50 °C with no exclusion of air or humidity, in the presence of F-TEDA (Selectfluor™) as an oxidant. The procedure is very functional

  (Ph 3 P)AuCl 被发现在芳基硼酸和芳基三氟硼酸钾的自偶联反应中是一种强大的催化剂，用于合成对称联芳基化合物。在 F-TEDA (Selectfluor™) 作为氧化剂存在下，反应在 96% EtOH 的台式反应条件下发生，温度介于室温和 50 °C 之间，不排除空气或湿气。该过程具有很强的官能团耐受性，并以高产率和大底物范围（26 个例子）提供相应的联芳基化合物。
• Room-temperature base-free copper-catalyzed trifluoromethylation of organotrifluoroborates to trifluoromethylarenes
  作者：Yuanyuan Huang、Xin Fang、Xiaoxi Lin、Huaifeng Li、Weiming He、Kuo-Wei Huang、Yaofeng Yuan、Zhiqiang Weng

  DOI：10.1016/j.tet.2012.09.083

  日期：2012.12

  An efficient room temperature copper-catalyzed trifluoromethylation of organotrifluoroborates under the base free condition using an electrophilic trifluoromethylating reagent is demonstrated. The corresponding trifluoromethylarenes were obtained in good to excellent yields and the reaction tolerates a wide range of functional groups. (C) 2012 Elsevier Ltd. All rights reserved.
• Organocatalyzed Asymmetric Conjugate Addition of Heteroaryl and Aryl Trifluoroborates: a Synthetic Strategy for Discoipyrrole D
  作者：Jiun‐Le Shih、Thien S. Nguyen、Jeremy A. May

  DOI：10.1002/anie.201503528

  日期：2015.8.17

  Bis‐heteroaryl or bis‐aryl stereocenters were formed by an organocatalytic enantioselective conjugate addition using the respective trifluoroborate salts as nucleophiles. Control studies suggested that fluoride dissociation is necessary in the anhydrous conditions. This strategy is applicable to the synthesis of discoipyrrole D, an inhibitor of BR5 fibroblast migration.

  使用相应的三氟硼酸盐作为亲核试剂，通过有机催化对映选择性共轭加成反应形成双-杂芳基或双-芳基立体中心。对照研究表明，在无水条件下氟化物离解是必要的。该策略适用于盘状吡咯D的合成，盘状吡咯D是BR5成纤维细胞迁移的抑制剂。
• 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.