| 1392513-28-8

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• CAS: 1392513-28-8
• 化学式: C₂₁H₂₉N₃OS*ClHO₄
• 分子量: 472.005
• InChiKey: LTSZVZFAFGLXFB-UHFFFAOYSA-N

反应信息

• 作为产物：
  描述：

  [Cu(III)(C14H21N(CH3)](ClO4)2 、 4-羟基苯硫酚 以 氘代乙腈 为溶剂， 以100%的产率得到
  参考文献：
  名称：

  Catalytic C–S, C–Se, and C–P Cross-Coupling Reactions Mediated by a Cu^I/Cu^III Redox Cycle

  摘要：

  A well-defined macrocyclic aryl-Cu-III complex (1) readily reacts with a series of R-SH, Ar-SH, Ar-SeH, and (RO)(2)(O)-PH (R = alkyl) nucleophiles to quantitatively afford the corresponding aryl alkyl thioethers, biaryl thioethers, biaryl selenide, and aryl dialkyl phosphonates, respectively. Competition experiments using bifunctional substrates revealed the important impact of lower pK(a) values in order to discriminate between functional groups, although other influencing parameters such as steric effects have been identified. The catalytic version of these reactions is achieved using aryl bromide and aryl chloride model substrates, affording C-S, C-Se, and C-P coupling compounds in excellent to moderate yields. Low-temperature UV-vis and NMR monitoring of the reactions of complex 1 with a variety of nucleophiles support the formation of a ground-state 1-nucleophile adduct. A mechanistic proposal for reaction of 1 with S-nucleophiles involving key nucleophile deprotonation and aryl-nucleophile reductive elimination steps is finally described.

  DOI：

  10.1021/om3006323