Methyl 4-(((4-chlorophenyl)sulfonyl)oxy)benzoate

• 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: Methyl 4-(((4-chlorophenyl)sulfonyl)oxy)benzoate
• 英文别名: Methyl 4-{[(4-chlorophenyl)sulfonyl]oxy}benzoate；methyl 4-(4-chlorophenyl)sulfonyloxybenzoate
• 化学式: C₁₄H₁₁ClO₅S
• 分子量: 326.757
• InChiKey: YOIVRGDQSHAJIX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  78
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Methyl 4-(((4-chlorophenyl)sulfonyl)oxy)benzoate 在 bis(triphenylphosphine)nickel(II) chloride 、 四乙基碘化铵 、 锌 作用下， 以 四氢呋喃 为溶剂， 以79%的产率得到联苯二甲酸二甲酯
  参考文献：
  名称：

  Aryl Mesylates in Metal-Catalyzed Homocoupling and Cross-Coupling Reactions. 1. Functional Symmetrical Biaryls from Phenols via Nickel-Catalyzed Homocoupling of Their Mesylates

  摘要：

  Aryl sulfonates including mesylate derived from phenols are converted in high yields to biaryls by homocoupling in the presence of catalytic amounts of zero-valent nickel catalysts generated in situ. This reaction provides the most convenient method for the synthesis of many functional symmetrical biaryls and was applied to the preparation of 2,2'-, 3,3'-, and 4,4'-disubstituted biphenyls and other biaryls. The influence of the electronic and steric effects of substituents attached in the ortho, meta, and para positions of aryl sulfonates and the nature of the sulfonate leaving group on the yield of homocoupled product as well as their influence on the extent of various side reactions were investigated. In addition, the influence of the effects of the polarity and dryness of solvent, halide ion source and concentration, and ratio of catalyst and ligand to aryl sulfonate are discussed.

  DOI：

  10.1021/jo00106a031
• 作为产物：
  描述：

  对羟基苯甲酸甲酯 、 4-氯苯磺酰氯 在 吡啶 作用下， 以83%的产率得到Methyl 4-(((4-chlorophenyl)sulfonyl)oxy)benzoate
  参考文献：
  名称：

  Aryl Mesylates in Metal-Catalyzed Homocoupling and Cross-Coupling Reactions. 1. Functional Symmetrical Biaryls from Phenols via Nickel-Catalyzed Homocoupling of Their Mesylates

  摘要：

  Aryl sulfonates including mesylate derived from phenols are converted in high yields to biaryls by homocoupling in the presence of catalytic amounts of zero-valent nickel catalysts generated in situ. This reaction provides the most convenient method for the synthesis of many functional symmetrical biaryls and was applied to the preparation of 2,2'-, 3,3'-, and 4,4'-disubstituted biphenyls and other biaryls. The influence of the electronic and steric effects of substituents attached in the ortho, meta, and para positions of aryl sulfonates and the nature of the sulfonate leaving group on the yield of homocoupled product as well as their influence on the extent of various side reactions were investigated. In addition, the influence of the effects of the polarity and dryness of solvent, halide ion source and concentration, and ratio of catalyst and ligand to aryl sulfonate are discussed.

  DOI：

  10.1021/jo00106a031

文献信息

• Aryl Mesylates in Metal-Catalyzed Homocoupling and Cross-Coupling Reactions. 1. Functional Symmetrical Biaryls from Phenols via Nickel-Catalyzed Homocoupling of Their Mesylates
  作者：Virgil Percec、Jin-Young Bae、Mingyang Zhao、Dale H. Hill

  DOI：10.1021/jo00106a031

  日期：1995.1

  Aryl sulfonates including mesylate derived from phenols are converted in high yields to biaryls by homocoupling in the presence of catalytic amounts of zero-valent nickel catalysts generated in situ. This reaction provides the most convenient method for the synthesis of many functional symmetrical biaryls and was applied to the preparation of 2,2'-, 3,3'-, and 4,4'-disubstituted biphenyls and other biaryls. The influence of the electronic and steric effects of substituents attached in the ortho, meta, and para positions of aryl sulfonates and the nature of the sulfonate leaving group on the yield of homocoupled product as well as their influence on the extent of various side reactions were investigated. In addition, the influence of the effects of the polarity and dryness of solvent, halide ion source and concentration, and ratio of catalyst and ligand to aryl sulfonate are discussed.