di-tert-butyl(ferrocenylmethyl)phosphine | 323580-95-6

• 分子结构分类: 有机化合物 - 碳氢化合物 - 芳香烃
• 英文名称: di-tert-butyl(ferrocenylmethyl)phosphine
• 英文别名: di-t-butyl(ferrocenylmethyl)phosphine；cyclopenta-1,3-diene;ditert-butyl(cyclopenta-1,3-dien-1-ylmethyl)phosphane;iron(2+)
• CAS: 323580-95-6
• 化学式: C₁₉H₂₉FeP
• 分子量: 344.26
• InChiKey: KOGBRCXDLGSKBP-UHFFFAOYSA-N

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：

  di-tert-butyl(ferrocenylmethyl)phosphine 、 (R)-di-μ-chlorobis[2-[1-amino-2,2-dimethylpropyl]phenyl-C,N]dipalladium(II) 以 甲苯 为溶剂， 以1%的产率得到
  参考文献：
  名称：

  环钯配体的不对称交换：光学活性磷钯环的新途径

  摘要：

  开发了不对称形式的环钯配体交换反应。该程序涉及在非质子介质中使用前手性膦。带有伯氨基和 C* 立体中心处的大 But 取代基的苄胺酯钯环用作手性诱导剂。

  DOI：

  10.1007/s11172-006-0573-8
• 作为产物：
  描述：

  N,N-dimethylaminomethylferrocene 、 二-叔丁基膦 以 溶剂黄146 为溶剂， 以68%的产率得到di-tert-butyl(ferrocenylmethyl)phosphine
  参考文献：
  名称：

  Di-t-butyl(ferrocenylmethyl)phosphine: air-stability, structural characterization, coordination chemistry, and application to palladium-catalyzed cross-coupling reactions

  摘要：

  Di-t-butyl(ferrocenylmethyl)phosphine (1) has been isolated and structurally characterized. This ligand was found to be reasonably air stable as a solid and it has been shown to possess electron donating ability similar to that of tri-i-propylphosphine. A palladium catalyst bearing this ligand performed room temperature Suzuki-Miyaura coupling reactions with aryl bromides. Modest Heck coupling reactivity with aryl bromides was also observed at 100 degrees C. Complexation of 1 with Pd-2(dba)(3) led to formation of (1)(2)Pd-0. Addition of 4-bromoanisole to solutions containing both 1 and Pd-2(dba)(3) led to formation of an oxidative addition product when 1:Pd ratios were <= 1. With a 2:1 ratio of 1:Pd, monophosphine complex formation and oxidative addition were significantly inhibited. (c) 2004 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2004.12.022
• 作为试剂：
  描述：

  4-溴苯甲醚 、 2-甲基苯硼酸 在 tris(dibenzylideneacetone)dipalladium (0) di-tert-butyl(ferrocenylmethyl)phosphine 、 caesium carbonate 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以70%的产率得到4-甲氧基-2-甲基-联苯
  参考文献：
  名称：

  Di-t-butyl(ferrocenylmethyl)phosphine: air-stability, structural characterization, coordination chemistry, and application to palladium-catalyzed cross-coupling reactions

  摘要：

  Di-t-butyl(ferrocenylmethyl)phosphine (1) has been isolated and structurally characterized. This ligand was found to be reasonably air stable as a solid and it has been shown to possess electron donating ability similar to that of tri-i-propylphosphine. A palladium catalyst bearing this ligand performed room temperature Suzuki-Miyaura coupling reactions with aryl bromides. Modest Heck coupling reactivity with aryl bromides was also observed at 100 degrees C. Complexation of 1 with Pd-2(dba)(3) led to formation of (1)(2)Pd-0. Addition of 4-bromoanisole to solutions containing both 1 and Pd-2(dba)(3) led to formation of an oxidative addition product when 1:Pd ratios were <= 1. With a 2:1 ratio of 1:Pd, monophosphine complex formation and oxidative addition were significantly inhibited. (c) 2004 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2004.12.022