(5-bromo-2-oxo-2H-pyran-3-yl)bis(triphenyl-l5-phosphaneyl)palladium(IV) bromide | 637007-05-7

• 英文名称: (5-bromo-2-oxo-2H-pyran-3-yl)bis(triphenyl-l5-phosphaneyl)palladium(IV) bromide
• CAS: 637007-05-7
• 化学式: C₄₁H₃₂Br₂O₂P₂Pd
• 分子量: 884.879
• InChiKey: CDHRJYDULJFLAB-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  None
• 重原子数：
  None
• 可旋转键数：
  None
• 环数：
  None
• sp3杂化的碳原子比例：
  None
• 拓扑面积：
  None
• 氢给体数：
  None
• 氢受体数：
  None

反应信息

• 作为产物：
  描述：

  C₄₁H₃₂Br₂O₂P₂Pd 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 (5-bromo-2-oxo-2H-pyran-3-yl)bis(triphenyl-l5-phosphaneyl)palladium(IV) bromide
  参考文献：
  名称：

  A Short Synthesis of Delavatine A Unveils New Insights into Site-Selective Cross-Coupling of 3,5-Dibromo-2-pyrone

  摘要：

  The recognition of latent symmetry in delavatine A has enabled a short synthesis of the natural product starting from 3,5,dibromo-2-pyrone. The concise synthetic route features a cascade process involving a 6 pi electrocyclization to construct the indane core of delavatine A. In addition, we have conducted detailed experimental and computational studies to gain an in-depth understanding of the mechanism of the observed site-selective cross-coupling of 3,5-dibromo-2-pyrone. This insight may provide new avenues to achieve the selective cross-coupling of multiply halogenated heteroarenes.

  DOI：

  10.1021/jacs.8b13012

文献信息

• Regioselectivity in the Stille Coupling Reactions of 3,5-Dibromo-2-pyrone
  作者：Won-Suk Kim、Hyung-Jin Kim、Cheon-Gyu Cho

  DOI：10.1021/ja037043a

  日期：2003.11.1

  C3, lower in electron density than C5, thus oxidative addition proceeds faster . When the reactions are carried out with Cu(I) in DMF or other polar aprotic solvent, however, the couplings occur predominantly at C5. The observed regiochemical reversal is attributed to the preferred formation of 5-pallado-2-pyrone intermediate which, in addition, turned out to be more reactive than 3-pallado-2-pyrone

  3,5-二溴-2-吡喃酮的Stille偶联通常在C3区域选择性地发生，电子密度低于C5，因此氧化加成进行得更快。然而，当在 DMF 或其他极性非质子溶剂中与 Cu(I) 进行反应时，偶联主要发生在 C5。观察到的区域化学逆转归因于 5-pallado-2-pyrone 中间体的优先形成，此外，它比 3-pallado-2-pyrone 中间体更具反应性。