Methyl 4-(((4-fluorophenyl)sulfonyl)oxy)benzoate | 161497-16-1

• 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-fluorophenyl)sulfonyl)oxy)benzoate
• 英文别名: p-Carbomethoxyphenyl p-fluorobenzenesulfonate；Methyl 4-(4-fluorophenyl)sulfonyloxybenzoate
• CAS: 161497-16-1
• 化学式: C₁₄H₁₁FO₅S
• 分子量: 310.303
• InChiKey: WWTQYWRCBHJWSM-UHFFFAOYSA-N

物化性质

• 沸点：
  444.2±45.0 °C(Predicted)
• 密度：
  1.377±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 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：
  6

反应信息

• 作为反应物：
  描述：

  Methyl 4-(((4-fluorophenyl)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85%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：

  4-氟苯磺酰氯 、 对羟基苯甲酸甲酯 在 吡啶 作用下， 以90%的产率得到Methyl 4-(((4-fluorophenyl)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. 2. Suzuki-Type Nickel-Catalyzed Cross-Coupling of Aryl Arenesulfonates and Aryl Mesylates with Arylboronic Acids
  作者：Virgil Percec、Jin-Young Bae、Dale H. Hill

  DOI：10.1021/jo00109a044

  日期：1995.2

  The Ni(O)-catalyzed Suzuki-type cross-coupling reaction of various aryl sulfonates including mesylate with arylboronic acids in the presence of K3PO4 is reported. The Ni(O) catalyst is generated in situ from NiCl2(dppf) and Zn. This novel reaction, which yields unsymmetrical biaryls in good yields under mild conditions, is highly regiospecific and tolerates various functional groups. The influence of the effects of the substituent of the aromatic substrates, the nature of the leaving group, solvent, and type of catalyst, and base on the reaction yield are discussed. The reactivity of various Ni(O) catalysts was compared to that of the less reactive Pd(O) catalysts.
• Percec Virgil, Bae Jin-Young, Zhao Mingyang, Hill Dale H., J. Org. Chem, 60 (1995) N 1, S 176-185
  作者：Percec Virgil, Bae Jin-Young, Zhao Mingyang, Hill Dale H.

  DOI：——

  日期：——
• 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.