N,N'-bis(diisopropylphosphino)dipyrromethane | 915218-02-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: N,N'-bis(diisopropylphosphino)dipyrromethane
• 英文别名: P2CH2；[2-[[1-Di(propan-2-yl)phosphanylpyrrol-2-yl]methyl]pyrrol-1-yl]-di(propan-2-yl)phosphane
• CAS: 915218-02-9
• 化学式: C₂₁H₃₆N₂P₂
• 分子量: 378.478
• InChiKey: CJTDWMJXMZULDN-UHFFFAOYSA-N

物化性质

• 沸点：
  450.8±55.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  9.9
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  N,N'-bis(diisopropylphosphino)dipyrromethane 在 (C₂H₅)3N 作用下， 以 甲苯 为溶剂， 生成 (PCHP)Pd(Me)
  参考文献：
  名称：

  Palladium Complexes of a P₂C Ligand Containing a Central Carbene Moiety

  摘要：

  Palladium(II) complexes of the PCHP pincer ligand were prepared from PdCl2, a "proto-pincer" P2CH2, and base. The resulting (PCHP)PdCl was converted to (PCHP)PdOTf. (PCHP)PdCl did not react with NaN(SiMe3)(2) but produced (PCHP)PdR (R = Me, Et, Ph) upon reaction with the corresponding organolithium, Grignard, or organozinc reagent. Trityl cation abstracted a hydride from (PCHP)PdCl to yield cationic Pd carbene complex (P2C)PdCl. Analysis of the structural data points to minimal pi-interaction between the carbene center and palladium.

  DOI：

  10.1021/om700414t

文献信息

• Double C−H Activation Results in Ruthenium Complexes of a Neutral PCP Ligand with a Central Carbene Moiety
  作者：Wei Weng、Sean Parkin、Oleg V. Ozerov

  DOI：10.1021/om060464r

  日期：2006.10.1

  Ru complexes of a new neutral PCP pincer ligand containing a central carbene ligand have been prepared (referred to as (P2C=) for emphasis). The ligand precursor P2CH2 can be prepared in good yield in two steps from pyrrole, formaldehyde, and chlorodiisopropylphosphine. The reaction between P2CH2 and [(p-cymene)RuCl2](2) in the presence of Et3N cleanly furnishes (P2C=) RuHCl. The latter possesses a Y-shaped five-coordinate geometry about Ru, as determined in an X-ray diffraction study. Reactions of (P2C=) RuHCl with a series of potential ligands have been examined. Addition of pyridine, MeCN, or ethylene leads to a simple adduct formation and addition of CO leads to coordination of two CO ligands to Ru with concomitant hydride-to-carbene migration, while addition of PMe3 gives rise to both types of products. (P2C=) RuHCl is a moderately active precatalyst for transfer hydrogenation of ketones. Addition of phenylacetylene leads to the insertion of the triple bond into Ru-H to give (P2C=)Ru(-CPh=CH2)Cl. (P2C=) RuHCl can be converted to (P2C=) RuCl2 by action of an iminium chloride reagent. (P2C=) RuCl2 adds one molecule of CO with retention of the carbene moiety, even at elevated temperatures. These results demonstrate the potential of (P2C=) as a robust and electronically distinctive ancillary ligand.
• Palladium Complexes of a P₂C Ligand Containing a Central Carbene Moiety
  作者：Wei Weng、Chun-Hsing Chen、Bruce M. Foxman、Oleg V. Ozerov

  DOI：10.1021/om700414t

  日期：2007.7.1

  Palladium(II) complexes of the PCHP pincer ligand were prepared from PdCl2, a "proto-pincer" P2CH2, and base. The resulting (PCHP)PdCl was converted to (PCHP)PdOTf. (PCHP)PdCl did not react with NaN(SiMe3)(2) but produced (PCHP)PdR (R = Me, Et, Ph) upon reaction with the corresponding organolithium, Grignard, or organozinc reagent. Trityl cation abstracted a hydride from (PCHP)PdCl to yield cationic Pd carbene complex (P2C)PdCl. Analysis of the structural data points to minimal pi-interaction between the carbene center and palladium.