2-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-4-fluorobenzonitrile

• 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: 2-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-4-fluorobenzonitrile
• 化学式: C₁₂H₁₃BFNO₂
• 分子量: 233.05
• InChiKey: LHPAFIZUHUYHHY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.47
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  42.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-4-fluorobenzonitrile 、 邻碘溴苯 在 bis-triphenylphosphine-palladium(II) chloride 、 tripotassium phosphate "n" hydrate 作用下， 以 甲苯 为溶剂， 反应 5.0h， 以65%的产率得到2'-bromo-5-fluoro-[1,1'-biphenyl]-2-carbonitrile
  参考文献：
  名称：

  Hydride-Induced Anionic Cyclization: An Efficient Method for the Synthesis of 6-H-Phenanthridines via a Transition-Metal-Free Process

  摘要：

  A novel procedure for hydride-induced anionic cyclization has been developed. It includes the reduction of a biaryl bromo-nitrile with a nucleophilic aromatic substitution (SNAr). A range of polysubstituted 6-H-phenanthridines were so obtained in moderate to good yield with good substrate tolerance. This method involves a concise transition-metal-free process and was applied to synthesize natural alkaloids.

  DOI：

  10.1021/acs.orglett.5b00544
• 作为产物：
  描述：

  硼酸三异丙酯 、 对氟苯腈 、 2,2-二甲基-1,3-丙二醇 在 2,2,6,6-四甲基哌啶 、 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 、 溶剂黄146 为溶剂， 反应 14.0h， 生成 2-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-4-fluorobenzonitrile
  参考文献：
  名称：

  Novel Syntheses of Fluorenones via Nitrile-Directed Palladium-Catalyzed C–H and Dual C–H Bond Activation

  摘要：

  Novel procedures for the [Pd]/[Ag]/TFA system catalyzed cascade reactions of nitrile directed remote C-H and dual C-H bond activation with insertion of nitrile were developed, which afforded variously polysubstituted fluorenones in moderate to good yields with tolerance of a wide variety of substrates.

  DOI：

  10.1021/ol401063w

文献信息

• Synthesis of Substituted 2-Cyanoarylboronic Esters
  作者：Morten Lysén、Henriette M. Hansen、Mikael Begtrup、Jesper L. Kristensen

  DOI：10.1021/jo052400g

  日期：2006.3.1

  [GRAPHICS]The synthesis of substituted 2-cyanoarylboronic esters is described via lithiation/in situ trapping of the corresponding methoxy-, trifluoromethyl-, fluoro-, chloro-, and bromobenzonitriles. The crude arylboronic esters were obtained in high yields and purities and with good regioselectivities.
• Novel Syntheses of Fluorenones via Nitrile-Directed Palladium-Catalyzed C–H and Dual C–H Bond Activation
  作者：Jung-Chih Wan、Jun-Min Huang、Yu-Huei Jhan、Jen-Chieh Hsieh

  DOI：10.1021/ol401063w

  日期：2013.6.7

  Novel procedures for the [Pd]/[Ag]/TFA system catalyzed cascade reactions of nitrile directed remote C-H and dual C-H bond activation with insertion of nitrile were developed, which afforded variously polysubstituted fluorenones in moderate to good yields with tolerance of a wide variety of substrates.
• Hydride-Induced Anionic Cyclization: An Efficient Method for the Synthesis of 6-<i>H</i>-Phenanthridines via a Transition-Metal-Free Process
  作者：Wei-Lin Chen、Chun-Yuan Chen、Yan-Fu Chen、Jen-Chieh Hsieh

  DOI：10.1021/acs.orglett.5b00544

  日期：2015.3.20

  A novel procedure for hydride-induced anionic cyclization has been developed. It includes the reduction of a biaryl bromo-nitrile with a nucleophilic aromatic substitution (SNAr). A range of polysubstituted 6-H-phenanthridines were so obtained in moderate to good yield with good substrate tolerance. This method involves a concise transition-metal-free process and was applied to synthesize natural alkaloids.