2,2,2-三氟乙烷-1-三氟硼酸钾 | 1510778-85-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 硼酸衍生物
• 中文名称: 2,2,2-三氟乙烷-1-三氟硼酸钾
• 英文名称: potassium β,β,β-trifluoroethyltrifluoroborate
• 英文别名: potassium 2,2,2-trifluoroethyltrifluoroborate；Potassium trifluoro(2,2,2-trifluoroethyl)borate；potassium;trifluoro(2,2,2-trifluoroethyl)boranuide
• CAS: 1510778-85-4
• 化学式: C₂H₂BF₆*K
• 分子量: 189.938
• InChiKey: VRCXHAGAWUNMMJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  10.0
• 可旋转键数：
  1.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  0.0

安全信息

• 危险性防范说明：
  P261,P280,P301+P312,P302+P352,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

反应信息

• 作为反应物：
  描述：

  2,2,2-三氟乙烷-1-三氟硼酸钾 、 2-氨基苯乙烯 在 四氯化硅 、 三乙胺 作用下， 以 甲苯 为溶剂， 反应 18.0h， 以21%的产率得到2-(β,β,β-trifluoroethyl)-2,1-borazaronaphthalene
  参考文献：
  名称：

  Accessing Molecularly Complex Azaborines: Palladium-Catalyzed Suzuki–Miyaura Cross-Couplings of Brominated 2,1-Borazaronaphthalenes and Potassium Organotrifluoroborates

  摘要：

  Despite their potential applications in both medicinal chemistry and materials science, there have been limited reports on the functionalization of 2,1-borazaronaphthalenes since their discovery in 1959. To access new chemical space and build molecular complexity, the Suzuki-Miyaura cross-coupling of brominated 2,1-borazaronaphthalenes been investigated. The palladium-catalyzed cross-coupling proceeds with an array of potassium (hetero)aryltrifluoroborates in high yield with low catalyst loadings under mild reaction conditions. By the use of a high-yielding bromination of various 2,1-borazaronaphthalenes to generate electrophilic azaborine species, a library of 3-(hetero)aryl and 3,6-diaryl-2,1-borazaronaphthalenes has been synthesized.

  DOI：

  10.1021/jo5011894
• 作为产物：
  描述：

  potassium hydrogen difluoride 、 2-碘-1,1,1-三氟乙烷 、 联硼酸频那醇酯 在 2nd Gen. precatalyst cataCXium® 、 potassium acetate 、 水 作用下， 以 二甲基亚砜 为溶剂， 以78%的产率得到2,2,2-三氟乙烷-1-三氟硼酸钾
  参考文献：
  名称：

  [EN] SYNTHESIS AND USE OF FLUORINATED COMPOUNDS
  [FR] SYNTHÈSE ET UTILISATION DE COMPOSÉS FLUORÉS

  摘要：

  本发明涉及氟化化合物的制备及其在有机合成中的用途。特别是，本发明涉及将结构式化合物与Rf-CH=N2或(CF3)2C=N2反应以形成全氟烷基或芳基化合物的 methods，以及由此反应得到的产品，其中X，YB和Rf如本文所述。

  公开号：

  WO2014126990A1

文献信息

• A Convergent, Modular Approach to Functionalized 2,1-Borazaronaphthalenes from 2-Aminostyrenes and Potassium Organotrifluoroborates
  作者：Steven R. Wisniewski、Courtney L. Guenther、O. Andreea Argintaru、Gary A. Molander

  DOI：10.1021/jo402616w

  日期：2014.1.3

  Azaborines are an important class of compounds with applications in both medicinal chemistry and materials science. The first borazaronaphthalene, 2-chloro-2,1-borazaronaphthalene, was reported in 1959; however, access to more highly functionalized substructures has been limited because of the harsh reaction conditions required to displace the chloride on boron. A convergent approach has been developed to synthesize disubstituted 2,1-borazaronaphthalenes from N-substituted 2-aminostyrenes and potassium organotrifluoroborates, where the potassium organotrifluoroborate is converted to the active R-BX2 species (X = Cl or F) in situ by addition of a fluorophile. Starting from aryl-, heteroaryl-, alkynyl-, alkenyl-, and alkyltrifluoroborates, a library of highly functionalized 2,1-borazaronaphthalenes were synthesized in one step under mild, transition-metal-free conditions.