3-MeC6H3-2-OP(i-Pr)2 | 874808-04-5

• 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: 3-MeC6H3-2-OP(i-Pr)2
• 英文别名: (3-Methylphenoxy)-di(propan-2-yl)phosphane
• CAS: 874808-04-5
• 化学式: C₁₃H₂₁OP
• 分子量: 224.283
• InChiKey: JXKLPUMCWJXHNL-UHFFFAOYSA-N

物化性质

• 沸点：
  283.6±33.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-MeC6H3-2-OP(i-Pr)2 以 甲醇 、 水 、 甲苯 为溶剂， 生成 [(4-MeC6H3-2-OP(i-Pr)2)Pd(H2O)2]BF4
  参考文献：
  名称：

  pH-Dependent C−C Coupling Reactions Catalyzed by Water-Soluble Palladacyclic Aqua Catalysts in Water

  摘要：

  The series of water-soluble palladacyclic aqua complexes [('Bu-SCS)Pd-II(H2O)](+) ([1](+), 'Bu-SCS = C6H3-2,6-(CH2S'Bu)(2)), [(Pr-i-SCS)Pd-II(H2O)](+) ([2](+), Pr-i-SCS = C6H3-2,6-((CH2SPr)-Pr-i)(2)), [(PCP)Pd-II(H2O)](+) ([3](+), PCP = C6H3-2,6-((OPPr2)-Pr-i)(2)), and [(PC)Pd-II(H2O)(2)](+) ([4](+), PC = 4-MeC6H3-2-((OPPr2)-Pr-i)) have been synthesized from the reaction of the corresponding palladacyclic chloro complexes with silver salts in water to optimize the catalytic activity for pH-dependent C-C coupling reactions in water by changing the supporting ligands from S-supporting (SCS) to P-supporting (PCP) ligands and also from tridentate (PCP) to bidentate (PC) ligands. It was confirmed that there was no precipitation of palladium black L under the present reaction conditions. The PC palladacyclic aqua complex [4](+) exhibits the highest catalytic activity among the water-soluble palladacyclic aqua complexes [1](+)-[4](+) for the pH-dependent Suzuki-Miyaura, Mizoroki-Heck, and Stille coupling reactions in water. This is one of the highest catalytic activities ever reported for coupling reactions with water-soluble palladium catalysts in water. The catalytic ability of the palladacyclic aqua catalysts is drastically dependent on the pH of the solution and the structures of supporting ligands. The structures of palladacyclic aqua and chloro complexes were unequivocally determined by X-ray analysis.

  DOI：

  10.1021/om0503592
• 作为产物：
  描述：

  氯二异丙基膦 、 间甲酚 在 三乙胺 作用下， 以 甲苯 为溶剂， 反应 15.0h， 生成 3-MeC6H3-2-OP(i-Pr)2
  参考文献：
  名称：

  P-Directed Borylation of Phenols

  摘要：

  Internal borylation occurs upon activation of aryl di-isopropylphosphinite boranes with HNTf2 to give heterocyclic intermediates that can be reductively quenched to afford 6 or treated with KHF2 to give the phenolic potassium aryl trifluoroborate salts 10. The latter salts are useful for Pd-catalyzed coupling with aryl iodides under Molander conditions, provided that precautions are taken to remove the KNTf2 byproduct from the preceding KHF2 step.

  DOI：

  10.1021/ol303203m

文献信息

• pH-Dependent C−C Coupling Reactions Catalyzed by Water-Soluble Palladacyclic Aqua Catalysts in Water
  作者：Seiji Ogo、Yoshitaka Takebe、Keiji Uehara、Takayuki Yamazaki、Hidetaka Nakai、Yoshihito Watanabe、Shunichi Fukuzumi

  DOI：10.1021/om0503592

  日期：2006.1.1

  The series of water-soluble palladacyclic aqua complexes [('Bu-SCS)Pd-II(H2O)](+) ([1](+), 'Bu-SCS = C6H3-2,6-(CH2S'Bu)(2)), [(Pr-i-SCS)Pd-II(H2O)](+) ([2](+), Pr-i-SCS = C6H3-2,6-((CH2SPr)-Pr-i)(2)), [(PCP)Pd-II(H2O)](+) ([3](+), PCP = C6H3-2,6-((OPPr2)-Pr-i)(2)), and [(PC)Pd-II(H2O)(2)](+) ([4](+), PC = 4-MeC6H3-2-((OPPr2)-Pr-i)) have been synthesized from the reaction of the corresponding palladacyclic chloro complexes with silver salts in water to optimize the catalytic activity for pH-dependent C-C coupling reactions in water by changing the supporting ligands from S-supporting (SCS) to P-supporting (PCP) ligands and also from tridentate (PCP) to bidentate (PC) ligands. It was confirmed that there was no precipitation of palladium black L under the present reaction conditions. The PC palladacyclic aqua complex [4](+) exhibits the highest catalytic activity among the water-soluble palladacyclic aqua complexes [1](+)-[4](+) for the pH-dependent Suzuki-Miyaura, Mizoroki-Heck, and Stille coupling reactions in water. This is one of the highest catalytic activities ever reported for coupling reactions with water-soluble palladium catalysts in water. The catalytic ability of the palladacyclic aqua catalysts is drastically dependent on the pH of the solution and the structures of supporting ligands. The structures of palladacyclic aqua and chloro complexes were unequivocally determined by X-ray analysis.
• P-Directed Borylation of Phenols
  作者：Clément Cazorla、Timothy S. De Vries、Edwin Vedejs

  DOI：10.1021/ol303203m

  日期：2013.3.1

  Internal borylation occurs upon activation of aryl di-isopropylphosphinite boranes with HNTf2 to give heterocyclic intermediates that can be reductively quenched to afford 6 or treated with KHF2 to give the phenolic potassium aryl trifluoroborate salts 10. The latter salts are useful for Pd-catalyzed coupling with aryl iodides under Molander conditions, provided that precautions are taken to remove the KNTf2 byproduct from the preceding KHF2 step.