3.5-二甲基苯基三氟硼酸钾 | 929626-19-7

• 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: 3.5-二甲基苯基三氟硼酸钾
• 英文名称: potassium (3,5-dimethylphenyl)trifluoroborate
• 英文别名: potassium;(3,5-dimethylphenyl)-trifluoroboranuide
• CAS: 929626-19-7
• 化学式: C₈H₉BF₃*K
• 分子量: 212.064
• InChiKey: LEJKDJXQAFWEDJ-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：

  3.5-二甲基苯基三氟硼酸钾 在 sodium iodide 、 chloroamine-T 、 sodium hydroxide 作用下， 以 甲醇 、 水 、 四氢呋喃 为溶剂， 反应 0.33h， 生成 1-(123I)iodanyl-3,5-dimethylbenzene
  参考文献：
  名称：

  Radioiodination of polymer-supported organotrifluoroborates

  摘要：

  为了简化放射性标记化合物的纯化过程，我们研究了一种结合聚合物化学和有机三氟硼酸盐化学优势的新策略。研究发现，使用多种氧化剂（包括聚合物支持的氧化剂）可以成功地对容易制备的 Dowex 支持的有机三氟硼酸盐进行无载体添加的放射性碘化。Copyright © 2010 John Wiley & Sons, Ltd. All Rights Reserved.

  DOI：

  10.1002/jlcr.1837
• 作为产物：
  描述：

  间二甲苯 在 [Ir(COD)(OMe)]2 potassium hydrogen difluoride 、 4,4'-二叔丁基-2,2'-二吡啶 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 21.0h， 生成 3.5-二甲基苯基三氟硼酸钾
  参考文献：
  名称：

  One-Pot Synthesis of Arylboronic Acids and Aryl Trifluoroborates by Ir-Catalyzed Borylation of Arenes

  摘要：

  The synthesis of arylboronic acids and aryl trifluoroborates in a one-pot sequence by Ir-catalyzed borylation of arenes is reported. To prepare the arylboronic acids, the Ir-catalyzed borylation is followed by oxidative cleavage of the boronic ester with NaIO4. To prepare the aryltrifluoroborate, the Ir-catalyzed borylation is followed by displacement of pinacol by KHF2. These two-step sequences give products that are more reactive toward subsequent chemistry than the initially formed pinacol boronates.

  DOI：

  10.1021/ol062903o

文献信息

• An efficient and straightforward route to terminal vinyl sulfones via palladium-catalyzed Suzuki reactions of α-bromo ethenylsulfones
  作者：Yewen Fang、Meijuan Yuan、Juncong Zhang、Li Zhang、Xiaoping Jin、Ruifeng Li、Jinjian Li

  DOI：10.1016/j.tetlet.2016.02.065

  日期：2016.3

  A general and simple protocol for the synthesis of α-substituted alkenylsulfones has been developed firstly via palladium-catalyzed Suzuki reactions between α-bromo ethenylsulfones and organoborons. Using a catalyst composed of Pd(OAc)2 and SPhos, a variety of aryl, heteroaryl, and alkylboron reagents could efficiently couple with α-bromo ethenylsulfones under mild conditions. Moreover, it has been

  首先通过α-溴乙烯基砜与有机硼之间的钯催化的Suzuki反应，开发了一种合成α-取代的链烯基砜的通用且简单的方法。使用由Pd（OAc）2和SPhos组成的催化剂，各种芳基，杂芳基和烷基硼试剂可以在温和的条件下有效地与α-溴乙烯砜偶联。此外，首次证明了乙烯基砜被2-硝基苯磺酰肼的二酰亚胺平滑还原。
• 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。
• Pd-Catalysed Suzuki coupling of α-bromoethenylphosphonates with organotrifluoroborates: a general protocol for the synthesis of terminal α-substituted vinylphosphonates
  作者：Li Zhang、Yewen Fang、Xiaoping Jin、Housan Xu、Ruifeng Li、Hao Wu、Bin Chen、Yiming Zhu、Yi Yang、Zongming Tian

  DOI：10.1039/c7ob02267k

  日期：——

  and robust protocol for the synthesis of terminal α-substituted vinylphosphonates via Suzuki coupling of α-bromovinylphosphonates with organotrifluoroborates has been successfully developed. This method features broad substrate scope, great functional group compatibilities, and easy scale-up ability. In addition to easy access of nucleophiles, straightforward synthesis of electrophiles was also realized

  已经成功开发了通过α-溴乙烯基膦酸酯与有机三氟硼酸酯的Suzuki偶联合成末端α-取代的乙烯基膦酸酯的通用且鲁棒的方案。该方法具有广泛的底物范围，强大的官能团相容性和易于放大的能力。除了易于接近亲核试剂外，还以α-溴乙烯基膦酸二乙酯为起始原料，实现了亲电试剂的直接合成。使用Pd2（dba）3 / SPhos的组合作为催化剂，在温和条件下可以很好地获得一系列α-烷基，芳基，杂芳基和炔基取代的乙烯基膦酸酯。作为合成应用，末端乙烯基膦酸酯在可见光促进的吉斯反应中用作有效的迈克尔受体。
• Four-coordinate triarylborane synthesis <i>via</i> cascade B–Cl/C–B cross-metathesis and C–H bond borylation
  作者：Kai Yang、Guan Zhang、Qiuling Song

  DOI：10.1039/c8sc02281j

  日期：——

  We herein describe a tandem highly selective B–Cl/C–B cross-metathesis of two same or different arylboranes and C–H bond borylation to synthesize four-coordinate triarylboranes with broad substrate scope.

  我们在此描述了一种串联高选择性的B-Cl/C-B交叉醚交换反应，用于合成具有广泛底物范围的四配位三芳基硼烷和C-H键硼化。
• Thioethers as Directing Group for the Palladium-Catalyzed Direct Arylation of Arenes
  作者：Jinzhong Yao、Ming Yu、Yuhong Zhang

  DOI：10.1002/adsc.201200447

  日期：2012.11.26

  Thioethers have proven to be efficient directing groups for the arylation of arenes under palladium catalysis. The thioether group can be readily removed or converted to other functional groups. Kinetic isotopic effect studies reveal that the CH cleavage of arenes might be the turnover-limiting step.

  硫醚已被证明是在钯催化下芳烃芳基化的有效导向基团。硫醚基可以容易地除去或转化为其他官能团。动力学同位素效应研究表明，芳烃的CH裂解可能是限制营业额的步骤。