trans-iodo(2-thienyl)bis(triphenylphosphine)palladium(II) | 168097-43-6

• 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-iodo(2-thienyl)bis(triphenylphosphine)palladium(II)
• 英文别名: trans-[(2-thienyl)PdI(P(C6H5)3)2]；iodopalladium(1+);2H-thiophen-2-ide;triphenylphosphane
• CAS: 168097-43-6
• 化学式: C₄₀H₃₃IP₂PdS
• 分子量: 841.04
• InChiKey: GPNZKCNNQSKGPF-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

• 作为反应物：
  描述：

  trans-iodo(2-thienyl)bis(triphenylphosphine)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：

  2-碘噻吩 、 四(三苯基膦)钯 以 苯 为溶剂， 以72%的产率得到trans-iodo(2-thienyl)bis(triphenylphosphine)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

• Formation of ArPdXL(amine) Complexes by Substitution of One Phosphane Ligand by an Amine in <i>trans‐</i> ArPdX(PPh ₃ ) ₂ Complexes
  作者：Anny Jutand、Serge Négri、Anna Principaud

  DOI：10.1002/ejic.200400413

  日期：2005.2

  Amines (piperidine, morpholine, diisopropylamine, terbutylamine), which may be used as bases in copper-free palladium-catalyzed Sonogashira reactions, substitute one phosphane PPh3 in trans-ArPdX(PPh3)2 complexes (Ar = Ph, 4-NC–C6H4, 4-MeOC–C6H4, 2-thienyl; X = I, Br, Cl) to generate ArPdX(PPh3)(amine) complexes in a reversible reaction whose equilibrium constant is determined in chloroform, THF, and

  胺（哌啶、吗啉、二异丙胺、叔丁胺），可在无铜钯催化的 Sonogashira 反应中用作碱，在反式 ArPdX(PPh3)2 配合物（Ar = Ph，4-NC–C6H4）中取代一种磷烷 PPh3 , 4-MeOC– , 2-thienyl; X = I, Br, Cl) 在可逆反应中生成 ArPdX(PPh3)(amine) 络合物，其平衡常数在氯仿、THF 和 DMF 中确定。平衡常数取决于 Ar、X、碱度和胺的位阻。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)
• Xie, Yang; Tan, Geok Kheng; Yan, Yaw Kai, Journal of the Chemical Society, Dalton Transactions, 1999, # 5, p. 773 - 779
  作者：Xie, Yang、Tan, Geok Kheng、Yan, Yaw Kai、Vittal, Jagadese J.、Ng, Siu Choon、Hor, T. S. Andy

  DOI：——

  日期：——