(E)-(1,2-diphenylvinyl)boronic acid | 936641-27-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (E)-(1,2-diphenylvinyl)boronic acid
• 英文别名: (E)-1,2-diphenylethenylboronic acid；[(E)-1,2-diphenylethenyl]boronic acid
• CAS: 936641-27-9
• 化学式: C₁₄H₁₃BO₂
• 分子量: 224.067
• InChiKey: VEFOXSIUFCIVPN-KAMYIIQDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.24
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-(1,2-diphenylvinyl)boronic acid 在 C₅₀H₆₈Cl₂O₄Rh₂ 、 重水 、 caesium carbonate 作用下， 以 1,4-二氧六环 为溶剂， 反应 4.0h， 以94%的产率得到trans-Stilben
  参考文献：
  名称：

  Asymmetric conjugate addition of cis-2-arylethenylboronic acids catalyzed by chiral diene/rhodium complexes: 1,4-rhodium shift from alkenylrhodium to arylrhodium intermediates

  摘要：

  The reaction of (E)-1,2-diphenylethenylboronic acid 1 with 2-cyclohexenone in the presence of a chiral diene/rhodium catalyst (5 mol %) gave 3-[2-((E)-2-phenylethenyl)phenyl]cyclohexanone in 99% yield with 98.7% ee; the catalytic cycle involves a 1,4-rhodium shift from a 2-phenylethenylrhodium to an ortho-alkenylphenylrhodium intermediate. In the reaction of 1 with (E)-1-phenyl-2-buten-1-one, either the tandem 1,4-shift/arylation product or the direct alkenylation product is formed selectively by an appropriate choice of chiral diene ligand. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.03.004

文献信息

• Synthesis of Trisubstituted Alkenes via Direct Oxidative Arene–Alkene Coupling
  作者：Roderick C. Jones、Michał Gałęzowski、Donal F. O’Shea

  DOI：10.1021/jo401326f

  日期：2013.8.16

  2-disubstituted alkene oxidative couplings, providing an efficient route to trisubstituted alkenes. The acetonitrile cosolvent dramatically accelerates the rate of reaction, and an insoluble inorganic oxidant limits unwanted oxidation of substrates. The scope of this procedure is illustrated with arenes and alkenes containing electron-donating and -withdrawing substituents resulting in a general synthetic

  已确定将无机氧化剂与乙酸/乙腈溶剂组合使用是直接芳烃/ 1,2-二取代烯烃氧化偶联的最佳方法，从而提供了通往三取代烯烃的有效途径。乙腈助溶剂极大地加快了反应速度，并且不溶的无机氧化剂限制了底物的有害氧化。用含有给电子和吸电子取代基的芳烃和烯烃说明了该方法的范围，这导致了对三取代烯烃的一般合成策略。对反应成分的原位ESI-MS分析已确定了藤原-森谷催化循环中的关键Pd中间体。
• Asymmetric conjugate addition of cis-2-arylethenylboronic acids catalyzed by chiral diene/rhodium complexes: 1,4-rhodium shift from alkenylrhodium to arylrhodium intermediates
  作者：Keigo Sasaki、Tamio Hayashi

  DOI：10.1016/j.tetasy.2012.03.004

  日期：2012.3

  The reaction of (E)-1,2-diphenylethenylboronic acid 1 with 2-cyclohexenone in the presence of a chiral diene/rhodium catalyst (5 mol %) gave 3-[2-((E)-2-phenylethenyl)phenyl]cyclohexanone in 99% yield with 98.7% ee; the catalytic cycle involves a 1,4-rhodium shift from a 2-phenylethenylrhodium to an ortho-alkenylphenylrhodium intermediate. In the reaction of 1 with (E)-1-phenyl-2-buten-1-one, either the tandem 1,4-shift/arylation product or the direct alkenylation product is formed selectively by an appropriate choice of chiral diene ligand. (C) 2012 Elsevier Ltd. All rights reserved.