difluoro (pentafluorophenyl)borane | 830-49-9

• 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: difluoro (pentafluorophenyl)borane
• 英文别名: pentafluorophenyldifluoroborane；pentafluorophenylfluorophenyldifluoroborane；Pentafluorphenyl-bor-difluorid；Perfluorophenyl borane；difluoro-(2,3,4,5,6-pentafluorophenyl)borane
• CAS: 830-49-9
• 化学式: C₆BF₇
• 分子量: 215.866
• InChiKey: IAAKXIPQVRCQAY-UHFFFAOYSA-N

物化性质

• 沸点：
  104-105 °C
• 密度：
  1.47±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.02
• 重原子数：
  14
• 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：
  7

反应信息

• 作为反应物：
  描述：

  difluoro (pentafluorophenyl)borane 在 氢氟酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 六氟苯
  参考文献：
  名称：

  Xenon(IV)–Carbon Bond of [C₆F₅XeF₂]⁺; Structural Characterization and Bonding of [C₆F₅XeF₂][BF₄], [C₆F₅XeF₂][BF₄]·2HF, and [C₆F₅XeF₂][BF₄]·nNCCH ₃ (n = 1, 2); and the Fluorinating Properties of [C₆F₅XeF₂][BF₄]

  摘要：

  The [C6F5XeF2](+) cation is the only example of a Xe(IV)-C bond, which had only been previously characterized as its [BF4](-) salt in solution by multi-NMR spectroscopy. The [BF4](-) salt and its new CH3CN and HF solvates, [C6F5XeF2][BF4].1.5CH(3)CN and [C6F5XeF2[BF4].2HF, have now been synthesized and fully characterized in the solid state by low-temperature, single-crystal X-ray diffraction and Raman spectroscopy. Crystalline [C6F5XeF2][BF4] and [C6F5XeF2][BF4].1.5CH3CN were obtained from CH3CN/CH2Cl2 solvent mixtures, and [C6F5XeF2][BF4].2HF was obtained from anhydrous HF (aHF), where [C6F5XeF2][BF4].1.5CH3CN is comprised of an equimolar mixture of [C6F5XeF2][BF4].CH3CN and [C6F5XeF2][BF4].2CH3CN. The crystal structures show that the [C6F5XeF2](+) cation has two short contacts with the F atoms of [BF4](-) or with the F or N atoms of the solvent molecules, HF and CH3CN. The low-temperature solid-state Raman spectra of [C6F5XeF2][BF4] and C6F5IF2 were assigned with the aid of quantum-chemical calculations. The bonding in [C6F5XeF2](+), C6F5IF2, [C6F5XeF2][BF4], [C6F5XeF2][BF4].CH3CN, [C6F5XeF2][BF4].2CH(3)CN, and [C6F5XeF2][BF4].2HF was assessed with the aid of natural bond orbital analyses and molecular orbital calculations. The (129)Xe, (19)F, and (11)B NMR spectra of [C6F5XeF2][BF4] in aHF are reported and compared with the (19)F NMR spectrum of C6F5IF2, and all previously unreported J((129)Xe-(19)F) and J((19)F-(19)F) couplings were determined. The long-term solution stabilities of [C6F5XeF2][BF4] were investigated by (19)F NMR spectroscopy and the oxidative fluorinating properties of [C6F5XeF2][BF4] were demonstrated by studies of its reactivity with K[C6F5BF3], Pn(C6F5)(3) (Pn = P, As, or Bi), and C6F5X (X = Br or I).

  DOI：

  10.1021/ic501831j
• 作为产物：
  描述：

  二苯基汞 生成 difluoro (pentafluorophenyl)borane
  参考文献：
  名称：

  Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: B: B-Verb.9, 5.1.4, page 161 - 166

  摘要：

  DOI：
• 作为试剂：
  描述：

  苯乙烯 、 邻苯基苯酚 在 difluoro (pentafluorophenyl)borane 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 2-Phenyl-6-(1-phenylethyl)phenol 、 2-Phenyl-4-(1-phenylethyl)phenol
  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。
• Polyfluoroorganoboron-Oxygen Compounds. 4 [1] Lithium Pentafluorophenyltrimethoxyborate, Li[C6F5B(OMe)3], Reactions with Selected Electrophiles and Nucleophiles
  作者：Nicolay Yu. Adonin、Vadim V. Bardin、Ulrich Flörke、Hermann-Josef Frohn

  DOI：10.1002/zaac.200500083

  日期：2005.10

  Li[C6F5B(OMe)3] (1a) reacted with the electrophiles CD3C(O)CD3, CH3OD, CD3CN, CH3CN, HOC2H4OH, Br2, and I2 to give C6F5X (X = D, H, Br, I). The treatment of 1a with Me3SiCl or BF3 in CH2Cl2 and CCl3F or pentene resulted in C6F5B(OMe)2 or C6F5BF2, respectively. The attempted metathesis of 1a with KF or [Bu4N]Br in CH2Cl2 led to a mixture of M[(C6F5)2B(OMe)2] (2b,c, main product) and M[C6F5B(OMe)3] (1b

  Li [C6F5B (OMe) 3] (1a) 与亲电试剂 CD3C (O) CD3、CH3OD、CD3CN、CH3CN、HOC2H4OH、Br2 和 I2 反应得到 C6F5X（X = D、H、Br、I）。在 CH2Cl2 和 CCl3F 或戊烯中用 Me3SiCl 或 BF3 处理 1a 分别产生 C6F5B (OMe) 2 或 C6F5BF2。1a 与 KF 或 [Bu4N] Br 在 CH2Cl2 中的尝试复分解导致 M [(C6F5) 2B (OMe) 2] (2b, c, 主要产物) 和 M [C6F5B (OMe) 3] (1b, c，次要产品）（M = [Bu4N]，K）。即使在乙醚、THF、DME 或 TMEDA 盐的存在下，1a 也发生歧化为二芳基硼酸盐 [Li (L) n] [(C6F5) 2B (OMe) 2]（L = Et2O、THF、DME、TMEDA） [Li
• Reactivity of Lewis Basic Platinum Complexes Towards Fluoroboranes
  作者：Jürgen Bauer、Holger Braunschweig、Rian D. Dewhurst、Krzysztof Radacki

  DOI：10.1002/chem.201301056

  日期：2013.7.1

  detailed investigations into the interaction of Lewis acidic fluoroboranes, for example BF2Pf (Pf=perfluorophenyl) and BF2ArF (ArF=3,5‐bis(trifluoromethyl)phenyl), with Lewis basic platinum complexes such as [Pt(PEt3)3] and [Pt(PCy3)2] (Cy=cyclohexyl). Two presumed Lewis adducts could be identified in solution and corresponding secondary products of these Lewis adducts were characterized in the solid state

  我们在此报告了路易斯酸性氟硼烷（例如BF 2 Pf（Pf =全氟苯基）和BF 2 Ar F（Ar F = 3,5-双（三氟甲基）苯基））与Lewis碱性铂配合物的相互作用的详细研究。[Pt（PEt 3）3 ]和[Pt（PCy 3）2 ]（Cy ＝环己基）。可以在溶液中鉴定出两个推测的路易斯加合物，并以固态表征了这些路易斯加合物的相应副产物。此外，沮丧的路易斯对（FLP）的概念被应用于系统[Pt（BPf 3）（CH 2 CH 2）（dcpp）]（dcpp = 1,3-双（二环己基膦基）丙烷; Pf =全氟苯基）。最后，进行DFT计算以确定铂中心的Lewis碱和硼中心的Lewis酸之间的相互作用。此外，提出了将硼酸酯BF 3，BCl 3和BF 2 Ar F氧化添加到模型配合物[Pt（PMe 3）2 ]的几种可能机理。
• Syntheses, Solution Multi-NMR Characterization, and Reactivities of [C₆F₅Xe]⁺ Salts of Weakly Coordinating Borate Anions, [BY₄]^- (Y = CF₃, C₆F₅, CN, or OTeF₅)
  作者：Karsten Koppe、Vural Bilir、Hermann-J. Frohn、Hélène P. A. Mercier、Gary J. Schrobilgen

  DOI：10.1021/ic7010138

  日期：2007.10.1

  New examples of [C6F5Xe]+ salts of the weakly coordinating anions [B(CF3)4]-, [B(C6F5)4]-, [B(CN)4]-, and [B(OTeF5)4]- have been synthesized by metathesis reactions of [C6F5Xe][BF4] with the corresponding MI[BY4] salts (MI = K or Cs; Y = CF3, C6F5, CN, or OTeF5). The salts were characterized in solution by multi-NMR spectroscopy. Their stabilities in prototypic solvents (CH3CN and CH2Cl2) and decomposition

  弱配位阴离子[B（CF3）4]-，[B（C6F5）4]-，[B（CN）4]-和[B（OTeF5）4]-的[C6F5Xe] +盐的新实例具有通过[C6F5Xe] [BF4]与相应的MI [BY4]盐（MI = K或Cs； Y = CF3，C6F5，CN或OTeF5）的复分解反应合成α-己内酰胺。通过多NMR光谱法在溶液中表征这些盐。据报道它们在原型溶剂（CH3CN和CH2Cl2）和分解产物中的稳定性。研究了[BY4]-的配位性质对[C6F5Xe] +分解速率以及弱亲核[BF4]-离子存在的影响。研究了[C6F5Xe] [BY4]在不同配位能力的溶剂（CH3CN和CH2Cl2）中对C6H5F的亲电五氟苯基化作用，以及较强亲核试剂（氟化物和水）对五氟苯基化过程的影响。[C6F5Xe] +的19F和129Xe NMR谱的仿真提供了全套的芳基19F-19F和129Xe-19F偶合常数及其相对符号。本系列盐中[C6F5Xe]
• Explored routes to unknown polyfluoroorganyliodine hexafluorides, RFIF6
  作者：Hermann-Josef Frohn、Vadim V. Bardin

  DOI：10.1016/j.jfluchem.2010.07.005

  日期：2010.10

  Two routes to RFIF6 compounds were investigated: (a) the substitution of F by RF in IF7 and (b) the fluorine addition to iodine in RFIF4 precursors. For route (a) the reagents C6F5SiMe3, C6F5SiF3, [NMe4][C6F5SiF4], C6F5BF2, and 1,4-C6F4(BF2)2 were tested. C6F5IF4 and CF3CH2IF4 were used in route (b) and treated with the fluoro-oxidizers IF7, [O2][SbF6]/KF, and K2[NiF6]/KF. The observed sidestep reactions

  研究了制备R F IF 6化合物的两种途径：（a）在IF 7中用R F取代F，以及（b）在R F IF 4前体中向碘中添加氟。对于路线（a），试剂C 6 F 5 SiMe 3，C 6 F 5 SiF 3，[NMe 4 ] [C 6 F 5 SiF 4 ]，C 6 F 5 BF 2和1,4-C 6 F 4（BF 2）2经过测试。在路线（b）中使用了C 6 F 5 IF 4和CF 3 CH 2 IF 4，并用了氟氧化剂IF 7，[O 2 ] [SbF 6 ] / KF和K 2 [NiF 6 ] / KF进行了处理。 。讨论了在路线（a）和（b）情况下观察到的回避反应。的C相互作用6 ˚F 5的SiX 3（X = Me中，F），C 6 ˚F 5 BF 2，1,4-C 6 ˚F 4（BF 2）2与IF 7仅给出相应的环氟化产物，全氟化环己二烯和环己烯衍生物，而[NMe 4 ] [C 6 F 5 SiF