potassium ((2-ethoxyethoxy)methyl)trifluoroborate

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 硼酸衍生物
• 英文名称: potassium ((2-ethoxyethoxy)methyl)trifluoroborate
• 英文别名: Potassium;2-ethoxyethoxymethyl(trifluoro)boranuide
• 化学式: C₅H₁₁BF₃O₂*K
• 分子量: 210.046
• InChiKey: CJASKFVVEFWSEB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.57
• 重原子数：
  12
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5-溴嘧啶 、 potassium ((2-ethoxyethoxy)methyl)trifluoroborate 在 dipotassium hydrogenphosphate 、 氯化镍二甲氧基乙烷 、 bis[3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridyl]phenyl]iridium(1+); 2-(2-pyridyl)pyridine; hexafluorophosphate 、 4,4'-二叔丁基-2,2'-二吡啶 作用下， 以 1,4-二氧六环 、 N,N-二甲基乙酰胺 为溶剂， 反应 24.0h， 以60%的产率得到5-((2-ethoxyethoxy)methyl)pyrimidine
  参考文献：
  名称：

  Photoredox Cross-Coupling: Ir/Ni Dual Catalysis for the Synthesis of Benzylic Ethers

  摘要：

  Single-electron transmetalation has emerged as an enabling paradigm for the cross-coupling of C-sp(3) hybridized organotrifluoroborates. Cross-coupling of alpha-alkoxymethyl-trifluoroborates with aryl and heteroaryl bromides has been demonstrated by employing dual catalysis with a combination of an iridium photoredox catalyst and a Ni cross-coupling catalyst. The resulting method enables the alkoxymethylation of diverse (hetero)arenes under mild, room-temperature conditions.

  DOI：

  10.1021/acs.orglett.5b01463
• 作为产物：
  描述：

  (溴甲基)三氟硼酸钾 、 乙二醇乙醚 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 3.5h， 以58%的产率得到potassium ((2-ethoxyethoxy)methyl)trifluoroborate
  参考文献：
  名称：

  Photoredox Cross-Coupling: Ir/Ni Dual Catalysis for the Synthesis of Benzylic Ethers

  摘要：

  Single-electron transmetalation has emerged as an enabling paradigm for the cross-coupling of C-sp(3) hybridized organotrifluoroborates. Cross-coupling of alpha-alkoxymethyl-trifluoroborates with aryl and heteroaryl bromides has been demonstrated by employing dual catalysis with a combination of an iridium photoredox catalyst and a Ni cross-coupling catalyst. The resulting method enables the alkoxymethylation of diverse (hetero)arenes under mild, room-temperature conditions.

  DOI：

  10.1021/acs.orglett.5b01463

文献信息

• Photoredox Cross-Coupling: Ir/Ni Dual Catalysis for the Synthesis of Benzylic Ethers
  作者：Idris Karakaya、David N. Primer、Gary A. Molander

  DOI：10.1021/acs.orglett.5b01463

  日期：2015.7.2

  Single-electron transmetalation has emerged as an enabling paradigm for the cross-coupling of C-sp(3) hybridized organotrifluoroborates. Cross-coupling of alpha-alkoxymethyl-trifluoroborates with aryl and heteroaryl bromides has been demonstrated by employing dual catalysis with a combination of an iridium photoredox catalyst and a Ni cross-coupling catalyst. The resulting method enables the alkoxymethylation of diverse (hetero)arenes under mild, room-temperature conditions.