2,7-di(p-tolylthio)-9,9-dimethyl-9H-fluorene | 1263672-65-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: 2,7-di(p-tolylthio)-9,9-dimethyl-9H-fluorene
• 英文别名: 9,9-Dimethyl-2,7-bis[(4-methylphenyl)sulfanyl]fluorene
• CAS: 1263672-65-6
• 化学式: C₂₉H₂₆S₂
• 分子量: 438.657
• InChiKey: GRGYMJGVMZPVOP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.3
• 重原子数：
  31
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  50.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  indium tri(4-methylbenzenethiolate) 、 2,7-二溴-9,9-二甲基芴 在 palladium diacetate 、 N,N-二异丙基乙胺 、 4,5-双二苯基膦-9,9-二甲基氧杂蒽 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以81%的产率得到2,7-di(p-tolylthio)-9,9-dimethyl-9H-fluorene
  参考文献：
  名称：

  Synthesis of Di-, Tri-, and Tetrasulfides through Multifold Carbon−Sulfur Cross-Coupling Reactions with Indium Tri(organothiolates) in a One-Pot Procedure

  摘要：

  Pd-catalyzed multifold (2-, 3-, and 4-fold) carbon sulfur cross-coupling reaction of indium tri(organothiolates) with polybromonated aromatic and heteroaromatic compounds was developed in a one-pot procedure. Both 2,5-dibromopyridine and 2,6-dibromopyridine reacted with indium tri(organothiolates) (0.68 equiv) in the presence of 4 mol A of Pd(OAc)(2), 4.2 mol % of Xantphos, and 1 equiv of diisopropylethylamine (DIPEA), producing disulfides in good to excellent yields. These results indicate that indium tri(organothiolates) transfer all three alkyl- or arylthio groups attached to indium metal to electrophilic coupling partners. Indium tri(organothiolates) derived from alkyl thiol having a low boiling point, such as n-propyl, isopropyl, and tert-butyl thiol, acted as good nucleophilic coupling partners. In addition, indium tri(arylthiolates) derived from aryl thiols possessing an electron-withdrawing or -donating group on the aromatic ring participated well in the Pd-catalyzed multifold carbon sulfur cross-coupling reaction. 4,4'-Dibromo-1,1'-biphenyl, 9,10-dibromoanthracene, 2,4-dibromoanisole, 2,7-dibromo-9,9-dimethylfluorene, 3,4-dibromothiophene, 2,3-dibromothiophene, 2,2'-bithiophene, 1,3,5-tribromobenzene, and 1,2,4,5-tetrabromobenzene were converted smoothly to the corresponding di-, tri-, and tetrasulfides.

  DOI：

  10.1021/jo102441t

文献信息

• Synthesis of Di-, Tri-, and Tetrasulfides through Multifold Carbon−Sulfur Cross-Coupling Reactions with Indium Tri(organothiolates) in a One-Pot Procedure
  作者：Phil Ho Lee、Youngchul Park、Sangkyun Park、Euijae Lee、Sunggak Kim

  DOI：10.1021/jo102441t

  日期：2011.2.4

  Pd-catalyzed multifold (2-, 3-, and 4-fold) carbon sulfur cross-coupling reaction of indium tri(organothiolates) with polybromonated aromatic and heteroaromatic compounds was developed in a one-pot procedure. Both 2,5-dibromopyridine and 2,6-dibromopyridine reacted with indium tri(organothiolates) (0.68 equiv) in the presence of 4 mol A of Pd(OAc)(2), 4.2 mol % of Xantphos, and 1 equiv of diisopropylethylamine (DIPEA), producing disulfides in good to excellent yields. These results indicate that indium tri(organothiolates) transfer all three alkyl- or arylthio groups attached to indium metal to electrophilic coupling partners. Indium tri(organothiolates) derived from alkyl thiol having a low boiling point, such as n-propyl, isopropyl, and tert-butyl thiol, acted as good nucleophilic coupling partners. In addition, indium tri(arylthiolates) derived from aryl thiols possessing an electron-withdrawing or -donating group on the aromatic ring participated well in the Pd-catalyzed multifold carbon sulfur cross-coupling reaction. 4,4'-Dibromo-1,1'-biphenyl, 9,10-dibromoanthracene, 2,4-dibromoanisole, 2,7-dibromo-9,9-dimethylfluorene, 3,4-dibromothiophene, 2,3-dibromothiophene, 2,2'-bithiophene, 1,3,5-tribromobenzene, and 1,2,4,5-tetrabromobenzene were converted smoothly to the corresponding di-, tri-, and tetrasulfides.