trans-iodotolylbis(triphenylarsine)palladium(II) | 168252-28-6

• 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: trans-iodotolylbis(triphenylarsine)palladium(II)
• 英文别名: Iodopalladium(1+);methylbenzene;triphenylarsane；iodopalladium(1+);methylbenzene;triphenylarsane
• CAS: 168252-28-6；78637-66-8
• 化学式: C₄₃H₃₇As₂IPd
• 分子量: 936.934
• InChiKey: GMMZNGZZCVOGDR-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  7.08
• 重原子数：
  47
• 可旋转键数：
  6
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.02
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  trans-iodotolylbis(triphenylarsine)palladium(II) 以 苯 为溶剂， 生成
  参考文献：
  名称：

  Methyl/Phenyl Exchange between Palladium and a Phosphine Ligand. Consequences for Catalytic Coupling Reactions

  摘要：

  The methyl ligand of trans-CH3Pd(PPh(3))(2)I (1) exchanges with a phenyl from its PPh(3) ligand, initially giving PhPd(PPh(3))(PMePh(2))I (4). The PMePh(2) ligand of 4 then exchanges with a PPh(3) of 1 to give CH3Pd(PPh(3))(PMePh(2))I and with the PMePh(2) ligand of more 4 to give PhPd(PPh(3))(2)I and trans-PhPd(PMePh(2))(2)I. The observed rate constant for the disappearance of 1 is about 7 x 10(-5) s(-1) at 75 degrees C. The rearrangement is irreversible, does not involve a free phosphonium cation, and does not require phosphine dissociation. The rearrangement competes with transmetalation when 1 is treated with tin reagents, leading to coupling products incorporating phenyls from PPh(3). Relatively electropositive phosphine substituents seem reluctant to rearrange onto palladium.

  DOI：

  10.1021/ja00138a012
• 作为产物：
  描述：

  tris(dibenzylideneacetone)dipalladium*C6H6 、 三苯胂 、 4-碘甲苯 以 苯 为溶剂， 以73%的产率得到trans-iodotolylbis(triphenylarsine)palladium(II)
  参考文献：
  名称：

  Methyl/Phenyl Exchange between Palladium and a Phosphine Ligand. Consequences for Catalytic Coupling Reactions

  摘要：

  The methyl ligand of trans-CH3Pd(PPh(3))(2)I (1) exchanges with a phenyl from its PPh(3) ligand, initially giving PhPd(PPh(3))(PMePh(2))I (4). The PMePh(2) ligand of 4 then exchanges with a PPh(3) of 1 to give CH3Pd(PPh(3))(PMePh(2))I and with the PMePh(2) ligand of more 4 to give PhPd(PPh(3))(2)I and trans-PhPd(PMePh(2))(2)I. The observed rate constant for the disappearance of 1 is about 7 x 10(-5) s(-1) at 75 degrees C. The rearrangement is irreversible, does not involve a free phosphonium cation, and does not require phosphine dissociation. The rearrangement competes with transmetalation when 1 is treated with tin reagents, leading to coupling products incorporating phenyls from PPh(3). Relatively electropositive phosphine substituents seem reluctant to rearrange onto palladium.

  DOI：

  10.1021/ja00138a012

文献信息

• Methyl/Phenyl Exchange between Palladium and a Phosphine Ligand. Consequences for Catalytic Coupling Reactions
  作者：David K. Morita、J. K. Stille、Jack R. Norton

  DOI：10.1021/ja00138a012

  日期：1995.8

  The methyl ligand of trans-CH3Pd(PPh(3))(2)I (1) exchanges with a phenyl from its PPh(3) ligand, initially giving PhPd(PPh(3))(PMePh(2))I (4). The PMePh(2) ligand of 4 then exchanges with a PPh(3) of 1 to give CH3Pd(PPh(3))(PMePh(2))I and with the PMePh(2) ligand of more 4 to give PhPd(PPh(3))(2)I and trans-PhPd(PMePh(2))(2)I. The observed rate constant for the disappearance of 1 is about 7 x 10(-5) s(-1) at 75 degrees C. The rearrangement is irreversible, does not involve a free phosphonium cation, and does not require phosphine dissociation. The rearrangement competes with transmetalation when 1 is treated with tin reagents, leading to coupling products incorporating phenyls from PPh(3). Relatively electropositive phosphine substituents seem reluctant to rearrange onto palladium.