potassium 4-(but-3-enyl)phenyltrifluoroborate | 1086974-99-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: potassium 4-(but-3-enyl)phenyltrifluoroborate
• 英文别名: Potassium (4-(but-3-en-1-yl)phenyl)trifluoroborate；potassium;(4-but-3-enylphenyl)-trifluoroboranuide
• CAS: 1086974-99-3
• 化学式: C₁₀H₁₁BF₃*K
• 分子量: 238.102
• InChiKey: SOMVCXDAYSDTRI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.14
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 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：

  potassium 4-(but-3-enyl)phenyltrifluoroborate 、 三氟甲磺酸4-氰基苯基醚 在 9-borabicyclo[3.3.1]nonane dimer 、 potassium fluoride 、 palladium diacetate 、 2-二环己膦基-2'-(N,N-二甲胺)-联苯 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以72%的产率得到potassium 4-(4-(4-cyanophenyl)butyl)phenyltriflurorborate
  参考文献：
  名称：

  Orthogonal Reactivity in Boryl-Substituted Organotrifluoroborates

  摘要：

  A method was developed for the hydroboration of alkenyl-containing organotrifluoroborates to generate dibora intermediates. The reactivity differences between organotrifluoroborates and trialkylboranes facilitated the cross-coupling of the borane moiety of these intermediates in a highly chemoselective fashion with aryl halides, leaving the trifluoroborate intact for subsequent transformation. A one-pot hydroboration/two-directional cross-coupling sequence was also demonstrated, providing the fully elaborated products in good yields. These conditions were also amenable in the cross-coupling of trialkylboranes to halo-containing organotrifluoroborates. The stability of the trifluoroborate moiety to these conditions allows simple and efficient strategies for complex molecule construction.

  DOI：

  10.1021/ja807076d
• 作为产物：
  描述：

  4-(3-丁烯-1-基)溴苯 在 硼酸三异丙酯 、 叔丁基锂 、 potassium hydrogen difluoride 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 2.0h， 以85%的产率得到potassium 4-(but-3-enyl)phenyltrifluoroborate
  参考文献：
  名称：

  Orthogonal Reactivity in Boryl-Substituted Organotrifluoroborates

  摘要：

  A method was developed for the hydroboration of alkenyl-containing organotrifluoroborates to generate dibora intermediates. The reactivity differences between organotrifluoroborates and trialkylboranes facilitated the cross-coupling of the borane moiety of these intermediates in a highly chemoselective fashion with aryl halides, leaving the trifluoroborate intact for subsequent transformation. A one-pot hydroboration/two-directional cross-coupling sequence was also demonstrated, providing the fully elaborated products in good yields. These conditions were also amenable in the cross-coupling of trialkylboranes to halo-containing organotrifluoroborates. The stability of the trifluoroborate moiety to these conditions allows simple and efficient strategies for complex molecule construction.

  DOI：

  10.1021/ja807076d

文献信息

• 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.