1,3-bis(4-fluorophenylselenomethyl)benzene

• 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: 1,3-bis(4-fluorophenylselenomethyl)benzene
• 英文别名: 1,3-Bis[(4-fluorophenyl)selanylmethyl]benzene；1,3-bis[(4-fluorophenyl)selanylmethyl]benzene
• 化学式: C₂₀H₁₆F₂Se₂
• 分子量: 452.264
• InChiKey: HLEHLGRHLDFGDJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.02
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  双(乙腈)氯化钯(II) 、 1,3-bis(4-fluorophenylselenomethyl)benzene 以 N,N-二甲基乙酰胺 为溶剂， 反应 0.33h， 以93%的产率得到[1,3-bis(4-fluorophenylselenomethyl)phenyl]palladium(II) chloride
  参考文献：
  名称：

  “无磷” Mizoroki–Heck和Suzuki–Miyaura反应中的钯缓释预催化剂和纳米颗粒

  摘要：

  AbstractThe Mizoroki–Heck reaction of electron‐rich aryl iodides was studied using a phosphine‐free catalytic system with a broad range of pre‐catalysts of varied stability and structure based on organoselenium chelators. The application of the “mercury test” by observing the response of the catalytic systems studied not only to the addition, but also to the withdrawal of Hg allowed us to establish a critical role of nanoparticles in the operation of the phosphine‐free catalytic systems. A three‐stage mechanistic scheme involving a slow stage served by mononuclear Pd species, and the main fast stage served by Pd nanoparticles, and terminated by the nanoparticle decay is proposed as a general mechanistic paradigm for the phosphine‐free Mizoroki–Heck and the related Suzuki–Miyaura reactions.magnified image

  DOI：

  10.1002/adsc.201400562
• 作为产物：
  描述：

  4,4'-difluorodiphenyl diselenide 、 间二溴苄 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 5.0h， 以84%的产率得到1,3-bis(4-fluorophenylselenomethyl)benzene
  参考文献：
  名称：

  “无磷” Mizoroki–Heck和Suzuki–Miyaura反应中的钯缓释预催化剂和纳米颗粒

  摘要：

  AbstractThe Mizoroki–Heck reaction of electron‐rich aryl iodides was studied using a phosphine‐free catalytic system with a broad range of pre‐catalysts of varied stability and structure based on organoselenium chelators. The application of the “mercury test” by observing the response of the catalytic systems studied not only to the addition, but also to the withdrawal of Hg allowed us to establish a critical role of nanoparticles in the operation of the phosphine‐free catalytic systems. A three‐stage mechanistic scheme involving a slow stage served by mononuclear Pd species, and the main fast stage served by Pd nanoparticles, and terminated by the nanoparticle decay is proposed as a general mechanistic paradigm for the phosphine‐free Mizoroki–Heck and the related Suzuki–Miyaura reactions.magnified image

  DOI：

  10.1002/adsc.201400562

文献信息

• The Palladium Slow-Release Pre-Catalysts and Nanoparticles in the “Phosphine-Free” Mizoroki-Heck and Suzuki-Miyaura Reactions
  作者：Alexander S. Sigeev、Alexander S. Peregudov、Andrei V. Cheprakov、Irina P. Beletskaya

  DOI：10.1002/adsc.201400562

  日期：2015.2.9

  AbstractThe Mizoroki–Heck reaction of electron‐rich aryl iodides was studied using a phosphine‐free catalytic system with a broad range of pre‐catalysts of varied stability and structure based on organoselenium chelators. The application of the “mercury test” by observing the response of the catalytic systems studied not only to the addition, but also to the withdrawal of Hg allowed us to establish a critical role of nanoparticles in the operation of the phosphine‐free catalytic systems. A three‐stage mechanistic scheme involving a slow stage served by mononuclear Pd species, and the main fast stage served by Pd nanoparticles, and terminated by the nanoparticle decay is proposed as a general mechanistic paradigm for the phosphine‐free Mizoroki–Heck and the related Suzuki–Miyaura reactions.magnified image