mesityl nonaflate | 1305205-41-7

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 卤代烷
• 英文名称: mesityl nonaflate
• 英文别名: (2,4,6-Trimethylphenyl) 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonate
• CAS: 1305205-41-7
• 化学式: C₁₃H₁₁F₉O₃S
• 分子量: 418.28
• InChiKey: ISFWYFSTMUTIRD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  51.8
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  mesityl nonaflate 、 对甲苯磺酰胺 在 potassium phosphate 、 tris-(dibenzylideneacetone)dipalladium(0) 、 2-二-叔丁膦基-2',4',6'-三异丙基联苯 作用下， 以 2-甲基-2-丁醇 为溶剂， 以20%的产率得到N-mesityl-4-methylbenzenesulfonamide
  参考文献：
  名称：

  A General Method for Palladium-Catalyzed Reactions of Primary Sulfonamides with Aryl Nonaflates

  摘要：

  A general method for Pd-catalyzed sulfonamidation of aryl nonafluorobutanesulfonates (aryl nonaflates) is described. A biaryl phosphine ligand, t-BuXPhos, formed the most active catalyst, and K3PO4 in tert-amyl alcohol was found to be the optimal base solvent combination for the reaction. The reaction conditions were tolerant of various functional groups such as cyano, nitro, ester, aldehyde, ketone, chloride, carbamate, and phenol. Heterocyclic aryl nonaflates were found to be suitable coupling partners. High yields of the coupled products were obtained from the reactions between inherently disfavored substrates such as electron-rich nonaflates and electron-poor sulfonamides. Kinetic data suggest reductive elimination to be the rate-limiting step for the reaction. The only limitation of this methodology that we have identified is the inability of 2,6-disubstituted aryl nonaflates to efficiently participate in the reaction.

  DOI：

  10.1021/jo200443u
• 作为产物：
  描述：

  全氟丁基磺酰氟 、 2,4,6-三甲酚 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以87%的产率得到mesityl nonaflate
  参考文献：
  名称：

  A General Method for Palladium-Catalyzed Reactions of Primary Sulfonamides with Aryl Nonaflates

  摘要：

  A general method for Pd-catalyzed sulfonamidation of aryl nonafluorobutanesulfonates (aryl nonaflates) is described. A biaryl phosphine ligand, t-BuXPhos, formed the most active catalyst, and K3PO4 in tert-amyl alcohol was found to be the optimal base solvent combination for the reaction. The reaction conditions were tolerant of various functional groups such as cyano, nitro, ester, aldehyde, ketone, chloride, carbamate, and phenol. Heterocyclic aryl nonaflates were found to be suitable coupling partners. High yields of the coupled products were obtained from the reactions between inherently disfavored substrates such as electron-rich nonaflates and electron-poor sulfonamides. Kinetic data suggest reductive elimination to be the rate-limiting step for the reaction. The only limitation of this methodology that we have identified is the inability of 2,6-disubstituted aryl nonaflates to efficiently participate in the reaction.

  DOI：

  10.1021/jo200443u

文献信息

• A General Method for Palladium-Catalyzed Reactions of Primary Sulfonamides with Aryl Nonaflates
  作者：Shashank Shekhar、Travis B. Dunn、Brian J. Kotecki、Donna K. Montavon、Steven C. Cullen

  DOI：10.1021/jo200443u

  日期：2011.6.3

  A general method for Pd-catalyzed sulfonamidation of aryl nonafluorobutanesulfonates (aryl nonaflates) is described. A biaryl phosphine ligand, t-BuXPhos, formed the most active catalyst, and K3PO4 in tert-amyl alcohol was found to be the optimal base solvent combination for the reaction. The reaction conditions were tolerant of various functional groups such as cyano, nitro, ester, aldehyde, ketone, chloride, carbamate, and phenol. Heterocyclic aryl nonaflates were found to be suitable coupling partners. High yields of the coupled products were obtained from the reactions between inherently disfavored substrates such as electron-rich nonaflates and electron-poor sulfonamides. Kinetic data suggest reductive elimination to be the rate-limiting step for the reaction. The only limitation of this methodology that we have identified is the inability of 2,6-disubstituted aryl nonaflates to efficiently participate in the reaction.