| 203304-06-7

• CAS: 203304-06-7
• 化学式: C₂₅H₆BF₁₅O
• 分子量: 618.109
• InChiKey: XDENUKKFSWGTGM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  None
• 重原子数：
  None
• 可旋转键数：
  None
• 环数：
  None
• sp3杂化的碳原子比例：
  None
• 拓扑面积：
  None
• 氢给体数：
  None
• 氢受体数：
  None

反应信息

• 作为反应物：
  描述：

  以 氘代苯 为溶剂， 生成
  参考文献：
  名称：

  Synthesis and Solution and Solid-State Structures of Tris(pentafluorophenyl)borane Adducts of PhC(O)X (X = H, Me, OEt, NPrⁱ₂)

  摘要：

  Reaction of the highly electrophilic borane B(C6F5)(3) with the carbonyl Lewis bases benzaldehyde,acetophenone, ethyl benzoate, and N,N-diisopropylbenzamide led to isolation of the crystalline adducts 1-H, 1-Me, 1-OEt, and 1-NPr, respectively, in good to excellent yields(63-89%). Equilibrium measurements and exchange experiments indicated that the order of basicity (from highest to lowest) of these bases toward B(C6F5)(3) follows the order N,N-diisopropylbenzamide > benzaldehyde > acetophenone > ethylbenzoate. The solution and solid-state structures were probed to rationalize these observations. In solution, the borane coordinates to the carbonyl lone pair syn to H and Me in the aldehyde and ketone adducts, as indicated by H-1/F-19 NOE difference experiments. The same coordination geometry was observed in the solid state upon X-ray diffraction analysis of the two adducts. The added front strain associated with the ketone adduct (C-O-B = 133.6(3)degrees vs 126.7(5)degrees for the benzaldehyde complex) accounts for the observed order of basicity with these two bases. For ethyl benzoate and N,N-diisopropylbenzamide, the borane coordinates syn to the phenyl group in both solution and the solid state. In addition to the carbonyl oxygen-boron interaction, the two complexes engage in a pi-stacking interaction between one of the borane C6F5 rings and the syn phenyl group. In addition to the structural proof of this interaction in the solid state, variable-temperature F-19 NMR experiments suggest it is important in the solution structures of these adducts as well.

  DOI：

  10.1021/om9710327
• 作为产物：
  描述：

  三(五氟苯基)硼烷 以 正戊烷 为溶剂， 反应 16.5h， 生成
  参考文献：
  名称：

  Cyclopropane formation under frustrated Lewis pair conditions

  摘要：

  使用HB（C6F5）2与-CH2OSiMe3取代的丙烯基二间二苯基膦反应，发生了氢化硼/(C6F5)2BOSiMe3消除序列，得到了磷酰基甲基取代的环丙烷衍生物，可能是通过磷环中间体形成的。

  DOI：

  10.1039/c5cc09585a

文献信息

• B(C₆F₅)₃: A Lewis Acid that Brings the Light to the Solid State
  作者：Max M. Hansmann、Alicia López-Andarias、Eva Rettenmeier、Carolina Egler-Lucas、Frank Rominger、A. Stephen K. Hashmi、Carlos Romero-Nieto

  DOI：10.1002/anie.201508461

  日期：2016.1.18

  The straightforward coordination of the Lewis acid B(C6F5)3 to classical, non‐emitting aldehydes results in solid‐state photoluminescence. Variation of the electronic properties of the carbonyl moieties lead to the modulation of the solid‐state emission colors, covering the entire visible spectrum with quantum yields up to 0.64. Steady‐state spectroscopy in combination with X‐ray diffraction analysis

  路易斯酸B（C 6 F 5）3与经典的不发光醛的直接配位导致固态光致发光。羰基部分电子性质的变化导致固态发射颜色的调制，覆盖了整个可见光谱，量子产率高达0.64。稳态光谱结合X射线衍射分析和DFT计算证实，路易斯加合物之间的分子间相互作用是观察到的发光的原因。此外，后一种相互作用的改变还引起了显着的固态现象，例如压致变色现象。我们方法的多功能性和简便性促进了固态发光材料的未来发展。
• Mechanistic insight into the catalytic hydrogenation of nonactivated aldehydes with a Hantzsch ester in the presence of a series of organoboranes: NMR and DFT studies
  作者：Go Hamasaka、Hiroaki Tsuji、Masahiro Ehara、Yasuhiro Uozumi

  DOI：10.1039/c9ra01468c

  日期：——

  Mechanistic studies on the organoborane-catalyzed transfer hydrogenation of nonactivated aldehydes with a Hantzsch ester (diethyl-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate) as a synthetic NADH analogue were performed by NMR experiments and DFT calculations. In the reaction of benzaldehyde with the Hantzsch ester, the catalytic activity of tris[3,5-bis(trifluoromethyl)phenyl]borane was superior

  通过 NMR 实验和 DFT 计算，对以 Hantzsch 酯 (diethyl-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate) 作为合成 NADH 类似物的非活化醛的有机硼烷催化转移氢化进行了机理研究. 在苯甲醛与Hantzsch酯的反应中，三[3,5-双(三氟甲基)苯基]硼烷的催化活性优于其他硼烷催化剂，如三(五氟苯基)硼烷、三氟硼烷醚合物或三苯基硼烷。化学计量核磁共振实验表明，氢化过程通过硼烷催化剂活化醛，然后氢化物从 Hantzsch 酯转移到所得活化醛上进行。在硼烷催化剂存在下用 Hantzsch 酯加氢苯甲醛的 DFT 计算支持了反应途径，并说明了为什么三[3,5-双(三氟甲基)苯基]硼烷的催化活性高于其他硼催化剂. 硼催化剂与苯甲醛或苯甲醇反应中的缔合常数和吉布斯自由能1 H NMR 分析也表明了为什么三[3,5-双(三
• Activation of C–H Activation: The Beneficial Effect of Catalytic Amount of Triaryl Boranes on Palladium-Catalyzed C–H Activation
  作者：Orsolya Tischler、Zsófia Bokányi、Zoltán Novák

  DOI：10.1021/acs.organomet.5b01017

  日期：2016.3.14

  Herein we report a novel approach to the acceleration of palladium-catalyzed C-H activation reactions. We demonstrated that the utilization of electron-deficient triaryl boranes as Lewis acidic cocatalysts of palladium enables the directed cross dehydrogenative coupling of aldehydes and anilides under mild reaction conditions. Study of the kinetic profile of the transformation reveals a unique, unexpectedly long induction period of the transformation.