3-pivaloylaminophenylboronic acid | 182344-19-0

• 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: 3-pivaloylaminophenylboronic acid
• 英文别名: [3-(2,2-Dimethylpropanoylamino)phenyl]boronic acid
• CAS: 182344-19-0
• 化学式: C₁₁H₁₆BNO₃
• 分子量: 221.064
• InChiKey: BNENTWUJDKAEHG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.35
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  69.6
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-pivaloylaminophenylboronic acid 在 1-fluoro-2,4,6-trimethylpyridinium hexafluorophosphate 、 (tBuCN)2Cu*OTf 、 silver fluoride 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 18.0h， 生成 N-(3-氟-苯基)-2,2-二甲基-丙酰胺
  参考文献：
  名称：

  Copper-Mediated Fluorination of Arylboronate Esters. Identification of a Copper(III) Fluoride Complex

  摘要：

  A method for the direct conversion of arylboronate esters to aryl fluorides under mild conditions with readily available reagents is reported. Tandem reactions have also been developed for the fluorination of arenes and aryl bromides through arylboronate ester intermediates. Mechanistic studies suggest that this fluorination reaction occurs through facile oxidation of Cu(I) to Cu(III), followed by rate-limiting transmetalation of a bound arylboronate to Cu(III). Fast C-F reductive elimination is proposed to occur from an aryl- copper(III)-fluoride complex. Cu(III) intermediates have been generated independently and identified by NMR spectroscopy and ESI-MS.

  DOI：

  10.1021/ja310909q

文献信息

• The synthesis of polysubstituted indoles from 3-bromo-2-indolyl phosphates
  作者：Peter Polák、Tomáš Tobrman

  DOI：10.1039/c7ob01127j

  日期：——

  A novel methodology for the synthesis of functionalised indoles based on the cross-coupling reactions of 3-bromo-2-indolyl phosphates is described. The preparation involves the conversion of easily available 2-oxindoles to 3,3-dibromo-2-oxindoles followed by the Perkow reaction affording 3-bromo-2-indolyl phosphates. Then bromine atom is substituted regioselectively by the Suzuki coupling reaction

  描述了一种基于3-溴-2-吲哚磷酸酯的交叉偶联反应合成官能化吲哚的新方法。制备涉及将容易获得的2-氧吲哚转化为3，3-二溴-2-氧吲哚，然后进行Perkow反应，得到3-溴-2-吲哚基磷酸酯。然后通过Suzuki偶联反应将溴原子区域选择性地取代。我们观察到氯化铝促进了3-取代的-2-吲哚基磷酸与有机锌试剂的反应，最终提供了2,3-二取代的吲哚。由易于获得的物质合成生物活性分子证明了该方法的整体多样性和效率。
• Copper-Mediated Fluorination of Arylboronate Esters. Identification of a Copper(III) Fluoride Complex
  作者：Patrick S. Fier、Jingwei Luo、John F. Hartwig

  DOI：10.1021/ja310909q

  日期：2013.2.20

  A method for the direct conversion of arylboronate esters to aryl fluorides under mild conditions with readily available reagents is reported. Tandem reactions have also been developed for the fluorination of arenes and aryl bromides through arylboronate ester intermediates. Mechanistic studies suggest that this fluorination reaction occurs through facile oxidation of Cu(I) to Cu(III), followed by rate-limiting transmetalation of a bound arylboronate to Cu(III). Fast C-F reductive elimination is proposed to occur from an aryl- copper(III)-fluoride complex. Cu(III) intermediates have been generated independently and identified by NMR spectroscopy and ESI-MS.