3-[4,6-Bis(3-cyanophenyl)-1,3,5,2,4,6-trioxatriborinan-2-yl]benzonitrile | 1393640-41-9

• 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-[4,6-Bis(3-cyanophenyl)-1,3,5,2,4,6-trioxatriborinan-2-yl]benzonitrile
• 英文别名: 3-[4,6-bis(3-cyanophenyl)-1,3,5,2,4,6-trioxatriborinan-2-yl]benzonitrile
• CAS: 1393640-41-9
• 化学式: C₂₁H₁₂B₃N₃O₃
• 分子量: 386.778
• InChiKey: JBXZAJRAYFCVMY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.85
• 重原子数：
  30
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  99.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  吗啉-4-基苯甲酸酯 、 3-[4,6-Bis(3-cyanophenyl)-1,3,5,2,4,6-trioxatriborinan-2-yl]benzonitrile 在 potassium carbonate 作用下， 以 1,4-二氧六环 为溶剂， 反应 24.0h， 以91%的产率得到3-吗啉-4-苯甲腈
  参考文献：
  名称：

  Transition-Metal-Free Electrophilic Amination of Arylboroxines

  摘要：

  A transition-metal-free strategy to construct C(sp(2))-N bonds using arylboroxines and O-benzoyl hydroxylamines as coupling partners has been developed. This transformation provides a useful method to access various aromatic amines.

  DOI：

  10.1021/ol301912a
• 作为产物：
  描述：

  以 甲苯 为溶剂， 反应 1.5h， 生成 3-[4,6-Bis(3-cyanophenyl)-1,3,5,2,4,6-trioxatriborinan-2-yl]benzonitrile
  参考文献：
  名称：

  Transition-Metal-Free Electrophilic Amination of Arylboroxines

  摘要：

  A transition-metal-free strategy to construct C(sp(2))-N bonds using arylboroxines and O-benzoyl hydroxylamines as coupling partners has been developed. This transformation provides a useful method to access various aromatic amines.

  DOI：

  10.1021/ol301912a

文献信息

• Enantiospecific, Nickel-Catalyzed Cross-Couplings of Allylic Pivalates and Arylboroxines
  作者：Harathi D. Srinivas、Qi Zhou、Mary P. Watson

  DOI：10.1021/ol5016724

  日期：2014.7.3

  We have developed an enantiospecific, nickel-catalyzed cross-coupling of unsymmetric 1,3-disubstituted allylic pivalates with arylboroxines. The success of this reaction relies on the use of BnPPh2 as a supporting ligand for the nickel(0) catalyst and NaOMe as a base. This method shows excellent functional group tolerance and broad scope in both the allylic pivalate and arylboroxine, enabling the preparation of 1,3-diaryl allylic products in high yields with excellent levels of regioselectivity and stereochemical fidelity.
• Stereospecific, Nickel-Catalyzed Suzuki–Miyaura Cross-Coupling of Allylic Pivalates To Deliver Quaternary Stereocenters
  作者：Kelsey M. Cobb、Javon M. Rabb-Lynch、Megan E. Hoerrner、Alex Manders、Qi Zhou、Mary P. Watson

  DOI：10.1021/acs.orglett.7b02063

  日期：2017.8.18

  Recognizing the importance of all-carbon, quaternary stereocenters in complex molecule synthesis, a stereospecific, nickel-catalyzed cross-coupling of allylic pivalates with arylboroxines to deliver products equipped with quaternary stereocenters and internal alkenes was developed. The enantioenriched allylic pivalate starting materials are readily prepared, and a variety of functional groups can be incorporated on both the allylic pivalate and the arylboroxine. Additional advantages include the use of a commercially available and air-stable Ni(II) salt and BISBI ligand, mild reaction conditions, and high yields and ee's. The observed stereoinversion of this reaction is consistent with an open transition state in the oxidative addition step.
• Transition-Metal-Free Electrophilic Amination of Arylboroxines
  作者：Qing Xiao、Leiming Tian、Renchang Tan、Ying Xia、Di Qiu、Yan Zhang、Jianbo Wang

  DOI：10.1021/ol301912a

  日期：2012.8.17

  A transition-metal-free strategy to construct C(sp(2))-N bonds using arylboroxines and O-benzoyl hydroxylamines as coupling partners has been developed. This transformation provides a useful method to access various aromatic amines.