3-乙烯基苯基三氟硼酸钾 | 1616634-79-7

• 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-乙烯基苯基三氟硼酸钾
• 英文名称: potassium 3-vinylphenyltrifluoroborate
• 英文别名: Potassium 3-vinylphenyltrifluoroborate；potassium;(3-ethenylphenyl)-trifluoroboranuide
• CAS: 1616634-79-7
• 化学式: C₈H₇BF₃*K
• 分子量: 210.048
• InChiKey: ZNLLFXIXJWNYAI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.61
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 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-bromo-2-methyl-2,1-borazaronaphthalene 、 3-乙烯基苯基三氟硼酸钾 在 chloro[(tri-tert-butylphosphine)-2-(2-aminobiphenyl)]palladium (II) 、 caesium carbonate 作用下， 以 水 为溶剂， 反应 18.0h， 以71%的产率得到3-(3-vinylphenyl)-2-methyl-2,1-borazaronaphthalene
  参考文献：
  名称：

  Accessing Molecularly Complex Azaborines: Palladium-Catalyzed Suzuki–Miyaura Cross-Couplings of Brominated 2,1-Borazaronaphthalenes and Potassium Organotrifluoroborates

  摘要：

  Despite their potential applications in both medicinal chemistry and materials science, there have been limited reports on the functionalization of 2,1-borazaronaphthalenes since their discovery in 1959. To access new chemical space and build molecular complexity, the Suzuki-Miyaura cross-coupling of brominated 2,1-borazaronaphthalenes been investigated. The palladium-catalyzed cross-coupling proceeds with an array of potassium (hetero)aryltrifluoroborates in high yield with low catalyst loadings under mild reaction conditions. By the use of a high-yielding bromination of various 2,1-borazaronaphthalenes to generate electrophilic azaborine species, a library of 3-(hetero)aryl and 3,6-diaryl-2,1-borazaronaphthalenes has been synthesized.

  DOI：

  10.1021/jo5011894

文献信息

• Synthesis of Functionalized 1,3,2-Benzodiazaborole Cores Using Bench-Stable Components
  作者：Geraint H. M. Davies、Gary A. Molander

  DOI：10.1021/acs.joc.6b00435

  日期：2016.5.6

  including organotrifluoroborates, enabling a wider array of substrate analogues under facile reaction conditions. Furthermore, physical, structural, and electronic properties of these compounds were explored computationally to understand the influence of the B–N replacement on the structure, aromaticity, and isosteric viability of these analogues.

  通过将B–N单元代替C═C键插入芳族骨架中，创建了保留可比结构特征的新伪芳族结构单元，氮杂硼烷基序为开发核心等位基因提供了独特的机会。先前的合成1,3,2-苯并二氮杂硼烷核的合成路线已使用有机氯化硼和硼酸作为硼前体。本文开发的转化利用了完全稳定的起始原料，包括有机三氟硼酸盐，可在方便的反应条件下实现更广泛的底物类似物阵列。此外，通过计算探索了这些化合物的物理，结构和电子性质，以了解B–N替代物对这些类似物的结构，芳香性和等构活力的影响。
• Accessing 2-(Hetero)arylmethyl-, -allyl-, and -propargyl-2,1-borazaronaphthalenes: Palladium-Catalyzed Cross-Couplings of 2-(Chloromethyl)-2,1-borazaronaphthalenes
  作者：Gary A. Molander、Javad Amani、Steven R. Wisniewski

  DOI：10.1021/ol5030508

  日期：2014.11.21

  1-borazaronaphthalene has provided an opportunity to expand dramatically the functionalization of the azaborines. This azaborinyl building block can serve as the electrophile in palladium-catalyzed cross-coupling reactions to form sp3–sp and sp3–sp2 bonds. The cross-coupling reactions of 2-(chloromethyl)-2,1-borazaronaphthalene with potassium (hetero)aryl- and alkenyltrifluoroborates as well as terminal alkynes provides

  2-(氯甲基)-2,1-硼氮杂萘的合成为大幅扩展氮杂硼烷的功能化提供了机会。这种氮杂硼烷基结构单元可在钯催化的交叉偶联反应中用作亲电子试剂，以形成 sp 3 -sp 和 sp 3 -sp 2键。2-(氯甲基)-2,1-硼杂萘与（杂）芳基-和烯基三氟硼酸钾以及末端炔烃的交叉偶联反应提供了获得各种新型氮杂硼烷的途径，从而可以制备假苄基取代的氮杂硼烷库来自一种常见的原材料。
• Copper-mediated N-arylation of methyl 2-aminothiophene-3-carboxylate with organoboron reagents
  作者：Komal Rizwan、Idris Karakaya、Drew Heitz、Muhammad Zubair、Nasir Rasool、Gary A. Molander

  DOI：10.1016/j.tetlet.2015.10.080

  日期：2015.12

  A practical protocol for the synthesis of N-arylated methyl 2-aminothiophene-3-carboxylate has been developed via Chan Lam cross-coupling. The desired products were synthesized by cross-coupling of methyl 2-aminothiophene-3-carboxylate with both arylboronic acids and potassium aryltrifluoroborate salts in moderate to good yields. A broad range of functional groups was well tolerated. (C) 2015 Elsevier Ltd. All rights reserved.