difluoro(4-fluorophenyl)borane | 32038-77-0

• 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: difluoro(4-fluorophenyl)borane
• 英文别名: 4-fluorophenyldifluoroborane；p-Fluorphenylbordifluorid；p-FC6H4BF2；Difluoro-(4-fluorophenyl)borane；difluoro-(4-fluorophenyl)borane
• CAS: 32038-77-0
• 化学式: C₆H₄BF₃
• 分子量: 143.904
• InChiKey: LTKQOBOSIBSWOV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.46
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  五氟(二氟碘)苯 、 difluoro(4-fluorophenyl)borane 以 二氯甲烷 为溶剂， 以53%的产率得到(p-fluorophenyl)(pentafluorophenyl)iodonium tetrafluoroborate
  参考文献：
  名称：

  摘要：

  Aryl(pentafluorophenyl)iodoniumtetrafluoroborates [Ar'Ar "I][BF4] (Ar' = C6F5, Ar " = C6H5, o-C6H4F, m-C6H4F p-C6H4F, 2,6-C6H3F2, 3,5-C6H3F2, 2,4,6-C6H2F3, 3,4,5-C6H2F3, C6F5) are prepared in good yields and high purity by the reaction of C6F6IF2 with Ar " BF2 in CH2Cl2. This convenient method can be applied generally to many iodonium compounds. Thermal and spectroscopic properties (H-1, C-13, F-19 NMR, IR, Raman) are reported and discussed. The solid state structures of six iodonium compounds show significant cation-anion interactions which result in two different arrangements: a dimer with a 8-membered ring or polymers with infinite zigzag chains. Ab initio calculations on prototypes of aryliodonium cations show relations between the kind of the aryl group (C6H5 vs. C6F5) and structural parameters as well as charges. By means of F-19 NMR the sigma (1)- and sigma (R)-constants of the [C6F5I](+)-substituent are determined.

  DOI：

  10.1002/1521-3749(200011)626:11<2419::aid-zaac2419>3.0.co;2-k
• 作为产物：
  描述：

  4-氟苯基三氟硼酸钾 在 C₈H₁₅N₂⁽¹⁺⁾*AlCl₄^(1-)*AlCl₃ 作用下， 以 正己烷 为溶剂， 反应 2.0h， 生成 difluoro(4-fluorophenyl)borane
  参考文献：
  名称：

  New approach to the generation of aryldifluoroboranes–prospective acid catalysts of organic reactions

  摘要：

  A new approach for preparation of aromatic and fluoroaromatic difluoroboranes via the interaction between corresponding aryltrifluoroborates and ionic liquids containing tetrachloroaluminate-anion and aluminum chloride has been developed. Catalytic properties of obtained aryldifluoroboranes have been investigated in model reactions of phenols alkylation. The dependence of catalytic properties on both the nature of solvent used and the type of substituents in the aromatic ring of difluoroborane has been established.

  DOI：

  10.1016/j.mencom.2018.07.009
• 作为试剂：
  描述：

  苯乙烯 、 苯酚 在 difluoro(4-fluorophenyl)borane 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 (1-苯基乙基)-苯酚 、 1-(对羟基苯基)1-苯乙烷
  参考文献：
  名称：

  New approach to the generation of aryldifluoroboranes–prospective acid catalysts of organic reactions

  摘要：

  A new approach for preparation of aromatic and fluoroaromatic difluoroboranes via the interaction between corresponding aryltrifluoroborates and ionic liquids containing tetrachloroaluminate-anion and aluminum chloride has been developed. Catalytic properties of obtained aryldifluoroboranes have been investigated in model reactions of phenols alkylation. The dependence of catalytic properties on both the nature of solvent used and the type of substituents in the aromatic ring of difluoroborane has been established.

  DOI：

  10.1016/j.mencom.2018.07.009

文献信息

• Synthesis of Fluorine-Containing Aryl(halo)boranes from Potassium Aryl(fluoro)borates
  作者：V. V. Bardin、S. A. Prikhod’ko、M. M. Shmakov、A. Yu. Shabalin、N. Yu. Adonin

  DOI：10.1134/s1070363220010089

  日期：2020.1

  Fluorine-containing aryldihalogenoboranes have been obtained by the reaction of boron and aluminum chlorides and bromides with potassium aryltrifluoroborates K[ArBF3] under mild conditions. In a similar way, bis(pentafluorophenyl)halogenoboranes have been synthesized by the reaction with K[(C6F5)2BF2]. The reaction of K[C6F5BF3] with AlBr3 affords a mixture of C6F5BF2 and C6F5BCl2 due to fast conversion

  通过在温和的条件下使硼和氯化铝与溴化物与芳基三氟硼酸钾K [ArBF 3 ]反应，可获得含氟的芳基二卤化硼烷。以类似的方式，通过与K [（C 6 F 5）2 BF 2 ]的反应合成了双（五氟苯基）卤代硼烷。K [C 6 F 5 BF 3 ]与AlBr 3的反应产生C 6 F 5 BF 2和C 6 F 5 BCl 2的混合物，这是由于AlBr 3快速转化为AlBrCl2。计算了BCl 2和BBr 2组的感应和共振参数。
• (Fluoroorgano)fluoroboranes and -fluoroborates I: synthesis and spectroscopic characterization of potassium fluoroaryltrifluoroborates and fluoroaryldifluoroboranes
  作者：H.-J. Frohn、H. Franke、P. Fritzen、V.V. Bardin

  DOI：10.1016/s0022-328x(99)00690-7

  日期：2000.3

  A convenient preparation of K[ArBF3] (Ar= 2-C6H4F, 3-C6H4F, 4-C6H4F, 2,6-C6H3F2, 3,5-C6H3F2, 2,4,6-C6H2F3, 3,4,5-C6H2F3, 2,3,4,5-C6HF4 and C6F5) is offered and the IR and multinuclear NMR spectra of these salts are reported. Treatment of the trifluoroborate salts with BF3 in chlorocarbon solvents provides an easy synthetic route to the corresponding aryldifluoroboranes ArBF2. The multinuclear NMR spectra of ArBF2 are presented. The electron substituent effect of the [-BF3](-)-group shows this substituent as one of the strongest sigma-electron donors, while its pi-electron influence is negligible (sigma(I) = - 0.32, sigma(R) = - 0.07). (C) 2000 Elsevier Science S.A. All rights reserved.
• A first methodical approach to salts with unsymmetrical fluorophenyl(pentafluorophenyl)difluoroiodonium(V) cations [Rf(RF)IF2]+ (Rf=x-FC6H4, x=2, 3, 4; RF=C6F5)
  作者：Hermann-Josef Frohn、André Wenda、Ulrich Flörke

  DOI：10.1016/j.tet.2010.04.047

  日期：2010.7

  A promising approach to the unknown type of [Ar'(Ar)IF2]X salts is offered. x-FC6H4IF4 (x=2, 3, 4) reacts with C6F5BF2 in CH2Cl2 and forms [x-FC6H4(C6F5)IF2][BF4] salts in good yields. For [4-FC6H4(C6F5)IF2][BF4] the fluoro-oxidizer property is shown in reactions with weakly reducing agents like E(C6F5)(3) (E=P, As, Sb, Bi) and ArI (Ar=4-FC6H4, C6F5). The fluorine/aryl substitution method is also applied to the synthesis of [(4-FC6H4)(2)[F-2][BF4], an example with two identical aryl groups in the difluoroiodonium(V) moiety. (C) 2010 Elsevier Ltd. All rights reserved.
• New approach to the generation of aryldifluoroboranes–prospective acid catalysts of organic reactions
  作者：Mikhail M. Shmakov、Sergey A. Prikhod’ko、Vadim V. Bardin、Nicolay Yu. Adonin

  DOI：10.1016/j.mencom.2018.07.009

  日期：2018.7

  A new approach for preparation of aromatic and fluoroaromatic difluoroboranes via the interaction between corresponding aryltrifluoroborates and ionic liquids containing tetrachloroaluminate-anion and aluminum chloride has been developed. Catalytic properties of obtained aryldifluoroboranes have been investigated in model reactions of phenols alkylation. The dependence of catalytic properties on both the nature of solvent used and the type of substituents in the aromatic ring of difluoroborane has been established.
• ——
  作者：F. Bailly、P. Barthen、H.-J. Frohn、M. Köckerling

  DOI：10.1002/1521-3749(200011)626:11<2419::aid-zaac2419>3.0.co;2-k

  日期：2000.11

  Aryl(pentafluorophenyl)iodoniumtetrafluoroborates [Ar'Ar "I][BF4] (Ar' = C6F5, Ar " = C6H5, o-C6H4F, m-C6H4F p-C6H4F, 2,6-C6H3F2, 3,5-C6H3F2, 2,4,6-C6H2F3, 3,4,5-C6H2F3, C6F5) are prepared in good yields and high purity by the reaction of C6F6IF2 with Ar " BF2 in CH2Cl2. This convenient method can be applied generally to many iodonium compounds. Thermal and spectroscopic properties (H-1, C-13, F-19 NMR, IR, Raman) are reported and discussed. The solid state structures of six iodonium compounds show significant cation-anion interactions which result in two different arrangements: a dimer with a 8-membered ring or polymers with infinite zigzag chains. Ab initio calculations on prototypes of aryliodonium cations show relations between the kind of the aryl group (C6H5 vs. C6F5) and structural parameters as well as charges. By means of F-19 NMR the sigma (1)- and sigma (R)-constants of the [C6F5I](+)-substituent are determined.