4-bromo-N-[4-bromo-2-di(propan-2-yl)phosphanylphenyl]-2-di(propan-2-yl)phosphanyl-N-methylaniline | 779333-69-6

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 4-bromo-N-[4-bromo-2-di(propan-2-yl)phosphanylphenyl]-2-di(propan-2-yl)phosphanyl-N-methylaniline
• CAS: 779333-69-6
• 化学式: C₂₅H₃₇Br₂NP₂
• 分子量: 573.331
• InChiKey: UMSVCCVRZIBFQM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  30
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-bromo-N-[4-bromo-2-di(propan-2-yl)phosphanylphenyl]-2-di(propan-2-yl)phosphanyl-N-methylaniline 、 palladium diacetate 以 甲苯 为溶剂， 以83%的产率得到
  参考文献：
  名称：

  N−C Cleavage in Pincer PNP Complexes of Palladium

  摘要：

  Several new N-methylated diarylamine-based PNP pincer ligands have been prepared. The synthesis of these ligands is modular and allows incorporation of a variety of substituents that change the solubility and the stereoelectronic properties of the ligand as well as allow for the introduction of a sensitive F-19 NMR spectroscopic probe. The reactions of PN(Me)P ligands with PdX2 (X = Cl, OAc) initially proceed with formation of an adduct, (PN(Me)P)PdX2, that may exist in either the neutral or the ionic forms. These adducts are unreactive in the case of PPh2-bearing ligands, but with the more donating PPr2i-bearing ligands, the adduct evolves into square planar (PNP)PdX with irreversible loss of MeX. Thus, the feasibility of cleavage of an unstrained N-C bond by Pd-II is demonstrated. The N-C cleavage is accelerated by decreasing the solvent polarity. The mechanism may involve either N-C oxidative addition or a nucleophilic attack (external or internal) of X- on the Me group of the N-bound PN(Me)P ligand.

  DOI：

  10.1021/om049651k

文献信息

• N−C Cleavage in Pincer PNP Complexes of Palladium
  作者：Lei Fan、Lin Yang、Chengyun Guo、Bruce M. Foxman、Oleg V. Ozerov

  DOI：10.1021/om049651k

  日期：2004.9.1

  Several new N-methylated diarylamine-based PNP pincer ligands have been prepared. The synthesis of these ligands is modular and allows incorporation of a variety of substituents that change the solubility and the stereoelectronic properties of the ligand as well as allow for the introduction of a sensitive F-19 NMR spectroscopic probe. The reactions of PN(Me)P ligands with PdX2 (X = Cl, OAc) initially proceed with formation of an adduct, (PN(Me)P)PdX2, that may exist in either the neutral or the ionic forms. These adducts are unreactive in the case of PPh2-bearing ligands, but with the more donating PPr2i-bearing ligands, the adduct evolves into square planar (PNP)PdX with irreversible loss of MeX. Thus, the feasibility of cleavage of an unstrained N-C bond by Pd-II is demonstrated. The N-C cleavage is accelerated by decreasing the solvent polarity. The mechanism may involve either N-C oxidative addition or a nucleophilic attack (external or internal) of X- on the Me group of the N-bound PN(Me)P ligand.