(bis(4-fluorophenyl)methyl)diphenylphosphine oxide | 1507379-45-4

• 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: (bis(4-fluorophenyl)methyl)diphenylphosphine oxide
• 英文别名: 1-[Diphenylphosphoryl-(4-fluorophenyl)methyl]-4-fluorobenzene；1-[diphenylphosphoryl-(4-fluorophenyl)methyl]-4-fluorobenzene
• CAS: 1507379-45-4
• 化学式: C₂₅H₁₉F₂OP
• 分子量: 404.396
• InChiKey: AHPFYHJOOGGBEY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-氟氯苄 在 palladium diacetate 、 sodium hydride 、 4,5-双二苯基膦-9,9-二甲基氧杂蒽 、 sodium t-butanolate 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 反应 21.17h， 生成 (bis(4-fluorophenyl)methyl)diphenylphosphine oxide
  参考文献：
  名称：

  Palladium-Catalyzed α-Arylation of Benzylic Phosphine Oxides

  摘要：

  A novel approach to prepare diarylmethyl phosphine oxides from benzyl phosphine oxides via deprotonative cross-coupling processes (DCCP) is reported. The optimization of the reaction was guided by High-Throughput Experimentation (HTE) techniques. The Pd(OAc)(2)/Xantphos-based catalyst enabled the reaction between benzyl diphenyl or dicyclohexyl phosphine oxide derivatives and aryl bromides in good to excellent yields (51-91%).

  DOI：

  10.1021/ol403124g

文献信息

• Heteropolyacid-Catalyzed Phosphorylation of Secondary Aromatic Alcohols with H-Phosphine Oxides in DMC: A Simple Protocol for C–P Bond Formation
  作者：Hongfeng Zhuang、Peng Wan、Chengxia Miao、Yang Yang、Shuyan Liang、Feng Han

  DOI：10.1021/acs.joc.3c02409

  日期：2024.2.16

  We successfully achieved the phosphorylation of secondary aromatic alcohols with H-phosphine oxides (less developed system) using phosphotungstic acid as a catalyst in dimethyl carbonate. The system was simple and environmentally friendly and showed better activity than traditional Lewis or Brønsted acids such as FeCl3, p-TsOH·H2O, etc., generating up to a 97% isolated yield. Control experiments indicated

  我们在碳酸二甲酯中使用磷钨酸作为催化剂，成功地实现了仲芳香醇与H-氧化膦（尚未开发的系统）的磷酸化。该体系简单、环保，比传统的路易斯酸或布朗斯台德酸如FeCl 3 、 p -TsOH·H 2 O等表现出更好的活性，分离收率高达97%。对照实验表明该反应不是通过自由基途径发生的，醚和碳正离子是该途径的关键中间体。
• Palladium-Catalyzed α-Arylation of Benzylic Phosphine Oxides
  作者：Sonia Montel、Tiezheng Jia、Patrick J. Walsh

  DOI：10.1021/ol403124g

  日期：2014.1.3

  A novel approach to prepare diarylmethyl phosphine oxides from benzyl phosphine oxides via deprotonative cross-coupling processes (DCCP) is reported. The optimization of the reaction was guided by High-Throughput Experimentation (HTE) techniques. The Pd(OAc)(2)/Xantphos-based catalyst enabled the reaction between benzyl diphenyl or dicyclohexyl phosphine oxide derivatives and aryl bromides in good to excellent yields (51-91%).