2-(2-(benzyloxy)phenyl)-5,5-dimethyl-1,3,2-dioxaborinane | 1239569-26-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-(2-(benzyloxy)phenyl)-5,5-dimethyl-1,3,2-dioxaborinane
• 英文别名: 5,5-Dimethyl-2-(2-phenylmethoxyphenyl)-1,3,2-dioxaborinane
• CAS: 1239569-26-6
• 化学式: C₁₈H₂₁BO₃
• 分子量: 296.174
• InChiKey: LHILUEQJEZSLJO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.03
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1-氯-2-苯基甲氧基苯 、 neopentylglycolborane 在 1,1'-双(二苯基膦)二茂铁 、 1,3-bis[(diphenylphosphino)propane]dichloronickel(II) 、 三乙胺 作用下， 以 甲苯 为溶剂， 以45%的产率得到2-(2-(benzyloxy)phenyl)-5,5-dimethyl-1,3,2-dioxaborinane
  参考文献：
  名称：

  Neopentylglycolborylation of ortho-Substituted Aryl Halides Catalyzed by NiCl₂-Based Mixed-Ligand Systems

  摘要：

  NiCl2-based mixed-ligand systems were shown to be very effective catalysts for the neopentylglycolborylation of aryl iodides, bromides, and chlorides bearing electron-rich and electron-deficient ortho-substituents. Although NiCl2-based single-ligand catalytic systems were able to mediate neopentylglycolborylation of selected substrates, they were not as effective for all substrates, highlighting the value of the mixed-ligand concept. Optimization of the Ni(II)-catalyzed neopentylglycolborylation of 2-iodoanisole and methyl 2-iodobenzoate demonstrated that, while the role of ligand and coligand in the conversion of Ni(II) precatalyst to Ni(0) active catalyst cannot be ignored, a mixed-ligand complex is likely present throughout the catalytic cycle. In addition, protodeborylation and hydrodehalogenation were demonstrated to be the predominant side reactions of borylation of ortho-substituted aryl halides containing the electron-deficient carboxylate substituents. Ni(II) complexes in the presence of H2O and Ni(0) are responsible for the catalysis of these side reactions.

  DOI：

  10.1021/jo101023t

文献信息

• Neopentylglycolborylation of <i>ortho</i>-Substituted Aryl Halides Catalyzed by NiCl₂-Based Mixed-Ligand Systems
  作者：Costel Moldoveanu、Daniela A. Wilson、Christopher J. Wilson、Pawaret Leowanawat、Ana-Maria Resmerita、Chi Liu、Brad M. Rosen、Virgil Percec

  DOI：10.1021/jo101023t

  日期：2010.8.20

  NiCl2-based mixed-ligand systems were shown to be very effective catalysts for the neopentylglycolborylation of aryl iodides, bromides, and chlorides bearing electron-rich and electron-deficient ortho-substituents. Although NiCl2-based single-ligand catalytic systems were able to mediate neopentylglycolborylation of selected substrates, they were not as effective for all substrates, highlighting the value of the mixed-ligand concept. Optimization of the Ni(II)-catalyzed neopentylglycolborylation of 2-iodoanisole and methyl 2-iodobenzoate demonstrated that, while the role of ligand and coligand in the conversion of Ni(II) precatalyst to Ni(0) active catalyst cannot be ignored, a mixed-ligand complex is likely present throughout the catalytic cycle. In addition, protodeborylation and hydrodehalogenation were demonstrated to be the predominant side reactions of borylation of ortho-substituted aryl halides containing the electron-deficient carboxylate substituents. Ni(II) complexes in the presence of H2O and Ni(0) are responsible for the catalysis of these side reactions.