(t-butyldimethylsilyloxymethyl)(p-methoxyphenyl)(p-tolyl)phosphine sulfide | 1420040-38-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (t-butyldimethylsilyloxymethyl)(p-methoxyphenyl)(p-tolyl)phosphine sulfide
• 英文别名: [Tert-butyl(dimethyl)silyl]oxymethyl-(4-methoxyphenyl)-(4-methylphenyl)-sulfidophosphanium；[tert-butyl(dimethyl)silyl]oxymethyl-(4-methoxyphenyl)-(4-methylphenyl)-sulfidophosphanium
• CAS: 1420040-38-5
• 化学式: C₂₁H₃₁O₂PSSi
• 分子量: 406.601
• InChiKey: BEYFMXDKBKWQMO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.41
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  19.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-碘氰基苯 、 (t-butyldimethylsilyloxymethyl)(p-methoxyphenyl)(p-tolyl)phosphine sulfide 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 、 1,1'-双(二苯基膦)二茂铁 、 cesium fluoride 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以99%的产率得到(p-cyanophenyl)(p-methoxyphenyl)(p-tolyl)phosphine sulfide
  参考文献：
  名称：

  Pd-Catalyzed P–C Cross-Coupling Reactions for Versatile Triarylphosphine Synthesis

  摘要：

  Practical and versatile syntheses of tertiary phosphine derivatives have been achieved by palladium-catalyzed deformylative P-C cross-coupling reactions of hydroxymethylphosphine derivatives. Sequential couplings of orthogonally protected precursors provide a simple and practical route toward a variety of tertiary phosphine derivatives having aryl substituents in any combination.

  DOI：

  10.1021/ol303448j
• 作为产物：
  描述：

  (benzoyloxymethyl)(t-butyldimethylsilyloxymethyl)(hydroxymethyl)phosphine sulfide 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 、 1,1'-双(二苯基膦)二茂铁 、 sodium ethanolate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 生成 (t-butyldimethylsilyloxymethyl)(p-methoxyphenyl)(p-tolyl)phosphine sulfide
  参考文献：
  名称：

  Pd-Catalyzed P–C Cross-Coupling Reactions for Versatile Triarylphosphine Synthesis

  摘要：

  Practical and versatile syntheses of tertiary phosphine derivatives have been achieved by palladium-catalyzed deformylative P-C cross-coupling reactions of hydroxymethylphosphine derivatives. Sequential couplings of orthogonally protected precursors provide a simple and practical route toward a variety of tertiary phosphine derivatives having aryl substituents in any combination.

  DOI：

  10.1021/ol303448j

文献信息

• Pd-Catalyzed P-C Cross-Coupling of Aryl Bromides and Triflates with Hydroxymethylphosphine Sulfide Derivatives
  作者：Hidetoshi Ohta、Qian Xue、Minoru Hayashi

  DOI：10.1002/ejoc.201701706

  日期：2018.2.14

  A powerful method for versatile phosphine synthesis: The P–C coupling of hydroxymethylphosphine sulfide derivatives with various aryl bromides and triflates to yield triarylphosphine sulfides has been developed. The new method was successfully applied to the sequential triple coupling of an orthogonally protected precursor to give an unsymmetrically substituted triarylphosphine sulfide.

  通用膦合成的有效方法：已开发了羟甲基膦硫化物衍生物与各种芳基溴化物和三氟甲磺酸酯进行P–C偶联以产生三芳基膦硫化物的方法。该新方法已成功应用于正交保护的前体的顺序三重偶联，从而得到不对称取代的三芳基膦硫化物。
• Pd-Catalyzed P–C Cross-Coupling Reactions for Versatile Triarylphosphine Synthesis
  作者：Minoru Hayashi、Takashi Matsuura、Ippei Tanaka、Hidetoshi Ohta、Yutaka Watanabe

  DOI：10.1021/ol303448j

  日期：2013.2.1

  Practical and versatile syntheses of tertiary phosphine derivatives have been achieved by palladium-catalyzed deformylative P-C cross-coupling reactions of hydroxymethylphosphine derivatives. Sequential couplings of orthogonally protected precursors provide a simple and practical route toward a variety of tertiary phosphine derivatives having aryl substituents in any combination.