potassium 4-(1-hydroxypropyl)phenyl trifluoroborate

• 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: potassium 4-(1-hydroxypropyl)phenyl trifluoroborate
• 英文别名: potassium 4-(1-hydroxypropyl)phenyltrifluoroborate；Potassium;trifluoro-[4-(1-hydroxypropyl)phenyl]boranuide
• 化学式: C₉H₁₁BF₃O*K
• 分子量: 242.09
• InChiKey: JYVNNSWDHCCDLN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.81
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  potassium 4-(1-hydroxypropyl)phenyl trifluoroborate 在 2-碘酰基苯甲酸 作用下， 以 丙酮 为溶剂， 反应 2.0h， 以74%的产率得到potassium 4-(1-propionyl)phenyltrifluoroborate
  参考文献：
  名称：

  Oxidation of Hydroxyl-Substituted Organotrifluoroborates

  摘要：

  Potassium- and tetra-n-butylammonium organotrifluoroborates containing hydroxyl groups have been prepared and oxidized using several common oxidants. Aryl-, alkenyl-, and alkyltrifluoroborates containing both primary and secondary hydroxyl groups were oxidized in moderate to excellent yields with complete retention of the trifluoroborate moiety. The utility of these oxidized products was demonstrated in a Suzuki-Miyaura cross-coupling reaction.

  DOI：

  10.1021/ja062974i
• 作为产物：
  描述：

  丙醛 、 4-溴苯基三氟硼酸钾 在 正丁基锂 、 potassium hydrogen bifluoride 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 3.25h， 以89%的产率得到potassium 4-(1-hydroxypropyl)phenyl trifluoroborate
  参考文献：
  名称：

  Oxidation of Hydroxyl-Substituted Organotrifluoroborates

  摘要：

  Potassium- and tetra-n-butylammonium organotrifluoroborates containing hydroxyl groups have been prepared and oxidized using several common oxidants. Aryl-, alkenyl-, and alkyltrifluoroborates containing both primary and secondary hydroxyl groups were oxidized in moderate to excellent yields with complete retention of the trifluoroborate moiety. The utility of these oxidized products was demonstrated in a Suzuki-Miyaura cross-coupling reaction.

  DOI：

  10.1021/ja062974i

文献信息

• Nickel-Catalyzed Cross-Coupling of Potassium Aryl- and Heteroaryltrifluoroborates with Unactivated Alkyl Halides
  作者：Gary A. Molander、O. Andreea Argintaru、Ioana Aron、Spencer D. Dreher

  DOI：10.1021/ol102717x

  日期：2010.12.17

  A method for the cross-coupling of alkyl electrophiles with various potassium aryl- and heteroaryltrifluoroborates has been developed. Nearly stoichiometric amounts of organoboron species could be employed to cross-couple a large variety of challenging heteroaryl nucleophiles. Several functional groups were tolerated on both the electrophilic and the nucleophilic partners. Chemoselective reactivity of C(sp(3))-Br bonds in the presence of C(sp(2))-Br bonds was achieved.
• Linchpin Synthons:  Metalation of Aryl Bromides Bearing a Potassium Trifluoroborate Moiety
  作者：Gary A. Molander、Noel M. Ellis

  DOI：10.1021/jo061324u

  日期：2006.9.1

  Aryl bromides bearing a potassium trifluoroborate moiety were subjected to lithium-halogen exchange at low temperature using a variety of alkyllithium reagents. A number of different electrophiles were evaluated in their reactions with the aryllithiums produced therein. Under carefully optimized conditions, potassium bromophenyl trifluoroborates afforded good to excellent yields of the corresponding alcohols (64-94% isolated yield) when aldehydes or ketones were used as the electophilic partner. Esters were unfortunately found to be unreactive.
• Oxidation of Hydroxyl-Substituted Organotrifluoroborates
  作者：Gary A. Molander、Daniel E. Petrillo

  DOI：10.1021/ja062974i

  日期：2006.8.1

  Potassium- and tetra-n-butylammonium organotrifluoroborates containing hydroxyl groups have been prepared and oxidized using several common oxidants. Aryl-, alkenyl-, and alkyltrifluoroborates containing both primary and secondary hydroxyl groups were oxidized in moderate to excellent yields with complete retention of the trifluoroborate moiety. The utility of these oxidized products was demonstrated in a Suzuki-Miyaura cross-coupling reaction.