(2-羟基-[1,1'-联苯基]-3-基)三氟硼酸钾 | 1033783-05-9

• 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-羟基-[1,1'-联苯基]-3-基)三氟硼酸钾
• 英文名称: potassium (2-hydroxy-[1,1'-biphenyl]-3-yl)trifluoroborate
• 英文别名: Potassium;trifluoro-(2-hydroxy-3-phenylphenyl)boranuide
• CAS: 1033783-05-9
• 化学式: C₁₂H₉BF₃O*K
• 分子量: 276.107
• InChiKey: MJJQEFMBXPFHMZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.12
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  碘苯 、 (2-羟基-[1,1'-联苯基]-3-基)三氟硼酸钾 在 四(三苯基膦)钯 、 potassium carbonate 作用下， 以 乙醇 、 水 、 甲苯 为溶剂， 以80%的产率得到2,6-二苯基苯酚
  参考文献：
  名称：

  P-Directed Borylation of Phenols

  摘要：

  Internal borylation occurs upon activation of aryl di-isopropylphosphinite boranes with HNTf2 to give heterocyclic intermediates that can be reductively quenched to afford 6 or treated with KHF2 to give the phenolic potassium aryl trifluoroborate salts 10. The latter salts are useful for Pd-catalyzed coupling with aryl iodides under Molander conditions, provided that precautions are taken to remove the KNTf2 byproduct from the preceding KHF2 step.

  DOI：

  10.1021/ol303203m
• 作为产物：
  描述：

  苯酚 在 四(三苯基膦)钯 、 potassium hydrogen difluoride 、 dimethyl sulfide borane 、 potassium carbonate 、 双三氟甲烷磺酰亚胺 、 三乙胺 作用下， 以 甲醇 、 氟苯 、 乙醇 、 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 72.0h， 生成 (2-羟基-[1,1'-联苯基]-3-基)三氟硼酸钾
  参考文献：
  名称：

  P-Directed Borylation of Phenols

  摘要：

  Internal borylation occurs upon activation of aryl di-isopropylphosphinite boranes with HNTf2 to give heterocyclic intermediates that can be reductively quenched to afford 6 or treated with KHF2 to give the phenolic potassium aryl trifluoroborate salts 10. The latter salts are useful for Pd-catalyzed coupling with aryl iodides under Molander conditions, provided that precautions are taken to remove the KNTf2 byproduct from the preceding KHF2 step.

  DOI：

  10.1021/ol303203m

文献信息

• Silyl-Directed, Iridium-Catalyzed <i>ortho</i>-Borylation of Arenes. A One-Pot <i>ortho</i>-Borylation of Phenols, Arylamines, and Alkylarenes
  作者：Timothy A. Boebel、John. F. Hartwig

  DOI：10.1021/ja8015878

  日期：2008.6.18

  regioselectivity of the borylation of arenes catalyzed by the combination of 4,4'-di-tert-butylbipyridine (dtbpy) and [Ir(cod)Cl]2 has typically been governed by steric effects. We describe a strategy that makes use of a new substituent for ortho-functionalization to overcome this bias. We show that arenes containing hydrosilyl substituents on an atom attached to the arene ring undergo borylation at the position

  由 4,4'-二叔丁基联吡啶 (dtbpy) 和 [Ir(cod)Cl]2 的组合催化的芳烃硼酸化的区域选择性通常受空间效应控制。我们描述了一种使用新取代基进行邻位官能化来克服这种偏见的策略。我们表明，在与芳烃环相连的原子上含有氢化硅烷基取代基的芳烃在氢化硅烷基的邻位位置发生硼化。使用铱催化从硅烷和苯酚或芳胺形成甲硅烷基醚和甲硅烷胺，我们已将邻硼酰化发展为将游离酚和单保护苯胺一锅法转化为羟基和氨基取代的有机硼衍生物。
• Boron-Selective Biaryl Coupling Approach to Versatile Dibenzoxaborins and Application to Concise Synthesis of Defucogilvocarcin M
  作者：Yuto Sumida、Ryu Harada、Tomoe Kato-Sumida、Kohei Johmoto、Hidehiro Uekusa、Takamitsu Hosoya

  DOI：10.1021/ol5031734

  日期：2014.12.5

  An efficient synthetic method for versatile dibenzoxaborins based on boron-selective Suzuki-Miyaura cross-coupling between o-borylphenols and aryl halides or triflates bearing a 1,8-diaminonaphthalene-protected o-boryl group is reported. A short synthesis of defucogilvocarcin M was achieved using the proposed method in combination with several other boron-mediated transformations.