tris(3-(methoxycarbonyl)phenyl)bismuth | 1365529-58-3

• 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: tris(3-(methoxycarbonyl)phenyl)bismuth
• 英文别名: Methyl 3-bis(3-methoxycarbonylphenyl)bismuthanylbenzoate；methyl 3-bis(3-methoxycarbonylphenyl)bismuthanylbenzoate
• CAS: 1365529-58-3
• 化学式: C₂₄H₂₁BiO₆
• 分子量: 614.408
• InChiKey: HJGGHGMHBNMOAZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.44
• 重原子数：
  31
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  78.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  tris(3-(methoxycarbonyl)phenyl)bismuth 、 3-氯-6-碘哒嗪 在 palladium diacetate 、 三苯基膦 、 cesium fluoride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以59%的产率得到3-chloro-6-(3-(methoxycarbonyl)phenyl)pyridazine
  参考文献：
  名称：

  三芳基或三杂芳基铋化合物与 3,6-二卤代哒嗪的 Pd 催化化学选择性交叉偶联反应

  摘要：

  3,6-二卤代哒嗪与三芳基-或三杂芳基铋化合物的交叉偶联反应在钯催化下进行。该反应具有高度化学选择性，以中等至良好的产率提供官能化的芳基-或杂芳基哒嗪基氯。

  DOI：

  10.1002/ejoc.201200977

文献信息

• Mechanism insight and scope of PEPPSI-catalyzed cross-coupling reaction between triarylbismuth and arylbromide
  作者：Bénédicte Cassirame、Sylvie Condon、Christophe Pichon

  DOI：10.1016/j.molcata.2016.07.016

  日期：2016.12

  In this paper we report the first cross-coupling reaction of Ar3Bi with Ar'X mediated by Pd-NHC complexes by keeping the ability of Ar3Bi to transfer the three aryl moieties. Investigations were carried out in order to minimize the quantity of the side product Ar-Ar coming from the conversion of Ar3Bi. The results showed that PEPPSI IPr was a good catalyst precursor. Efforts were focussed on the rule of each additive such as PPh3 and the base. It was notably found that the presence of PPh3 (ratio PEPPSI IPriPPh(3): 1/1) was essential to keep the process efficient. Therefore NHC-Pd-PPh3 has been assumed as being the catalytic species. Under the optimized reaction conditions the concomitant formation of the undesired biaryl side product was restricted to its inherent formation consecutive to the reduction of the catalyst precursor to Pd(0). In a last study, the scope and the limitation of the new catalytic methodology were examined and a large range of unsymmetrical biaryl compounds Ar-Ar' bearing various substituents from strongly electron-donating to electron-withdrawing ones have been prepared and fully characterized. (C) 2016 Elsevier B.V. All rights reserved.
• Pd-Catalyzed Chemoselective Cross-Coupling Reaction of Triaryl- or Triheteroarylbismuth Compounds with 3,6-Dihalopyridazines
  作者：Karène Urgin、Christophe Aubé、Muriel Pipelier、Virginie Blot、Christine Thobie-Gautier、Stéphane Sengmany、Jacques Lebreton、Eric Léonel、Didier Dubreuil、Sylvie Condon

  DOI：10.1002/ejoc.201200977

  日期：2013.1

  The cross-coupling reactions of 3,6-dihalopyridazines with triaryl- or triheteroarylbismuth compounds were performed under palladium catalysis. The reaction was highly chemoselective, affording functionalized aryl- or heteroarylpyridazinyl chlorides in moderate to good yields.

  3,6-二卤代哒嗪与三芳基-或三杂芳基铋化合物的交叉偶联反应在钯催化下进行。该反应具有高度化学选择性，以中等至良好的产率提供官能化的芳基-或杂芳基哒嗪基氯。