Fluor-diphenylsilan | 1013-91-8

• 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: Fluor-diphenylsilan
• 英文别名: Diphenylfluorsilan；fluoro(diphenyl)silane
• CAS: 1013-91-8
• 化学式: C₁₂H₁₁FSi
• 分子量: 202.303
• InChiKey: BUFRPMIIXBOSDW-UHFFFAOYSA-N

物化性质

• 沸点：
  92-93 °C(Press: 2 Torr)
• 密度：
  1.1072 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  1.49
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• 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：
  1

反应信息

• 作为反应物：
  描述：

  Fluor-diphenylsilan 在 hydridochlorotris(triphenylphosphine)ruthenium(II) 、 bis(η3-allyl-μ-chloropalladium(II)) 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 1.5h， 生成 4-甲基联苯
  参考文献：
  名称：

  Ruthenium-catalyzed hydrosilylation of terminal alkynes: stereodivergent synthesis of (E)- and (Z)-alkenylsilanes

  摘要：

  Stereodivergent hydrosilylation of terminal alkynes (RCequivalent toCH; R = Ph, p-tolyl, Cy, n-hexyl) with hydrosilanes (HSiMe2Ar; Arequivalent toPh, 3.5-(CF3)(2)C6H3, 4-CFC3H4, 4-MeOC6H4) has been examined using ruthenium catalysts. (E)-selective reactions giving (E)-RCH=CHSiMe2Ar proceed in over 99% selectivity in the presence of a catalytic amount of RuHCl(CO)(PPh3)(3). On the other hand, (Z)-selective reactions are successfully conducted in 91-99% selectivity by using Ru(SiMe2Ph)Cl(CO)(PPr'(3))(2) as the catalyst. All reactions readily proceed at room temperature in high yields. (E)- and (Z)-styrylsilanes having a SiMe2[C6H3-3,5-(CF3)(2)] group serve as good cross-coupling reagents with p-iodotoluene in the presence of tetrabutylammonium. fluoride and [Pd(eta(3)-al-lyl)Cl](2) catalyst. (C) 2002 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s0022-328x(01)01319-5
• 作为产物：
  描述：

  氯化二苯基硅烷 在 NH₄SiF₆ 作用下， 以 乙二醇二甲醚 为溶剂， 反应 0.5h， 以90%的产率得到Fluor-diphenylsilan
  参考文献：
  名称：

  1,3-二烯与二氟（苯基）硅烷的催化不对称氢化硅烷化

  摘要：

  具有光学活性配体的钯配合物可使用二氟（苯基）硅烷催化1,3-二烯的不对称氢化硅烷化反应，得到对映体过量的光学活性烯丙基二氟（苯基）硅烷。

  DOI：

  10.1016/0022-328x(95)00311-d

文献信息

• Darstellung und charakterisierung der phenylfluordisilane Si2Ph6-nFn
  作者：E. Hengge、F. Schrank

  DOI：10.1016/0022-328x(86)84027-x

  日期：1986.1

  Fluorination of chlorophenyldisilanes with ZnF2 yields the corresponding fluorophenyldisilanes, if silver powder is used as a catalyst. 1,2-Difluorotetraphenyldisilane is synthesized by UV irradiation of bis-(fluorodiphenylsilyl)mercury, the first known fluorosilylmercury compound. All the eight possible fluorophenyldisilanes, unknown up to now, are characterized by spectroscopic methods.

  如果将银粉用作催化剂，则用ZnF 2氟化氯苯基二硅烷会产生相应的氟苯基二硅烷。通过紫外线辐射双-（氟代二苯基甲硅烷基）汞（第一种已知的氟代甲硅烷基汞化合物）合成1,2-二氟四苯基乙硅烷。迄今为止，尚不知道的八种可能的氟苯基二硅烷都通过光谱法进行了表征。
• Square-Planar Iron(II) Silyl Complexes: Synthesis, Characterization, and Insertion Reactivity
  作者：C. Vance Thompson、Hadi D. Arman、Zachary J. Tonzetich

  DOI：10.1021/acs.organomet.9b00335

  日期：2019.8.12

  hyde to generate a new intermediate-spin complex assigned as [Fe(CH(OSiHPh2)Ar)(CyPNP)] (Ar = 4-CF3C6H4), corresponding to a 2,1-insertion of the aldehyde. Finally, the reaction of CO2 with [Fe(SiHPh2)(CyPNP)] resulted in reduction of CO2 to CO and formation of [Fe(CO)(SiHPh2)(CyPNP)]. The stoichiometric reactivity of this new class of iron silyl complexes indicates diverse insertion behavior applicable

  用2或3当量的膦处理[Fe（BH 4）（Cy PNP）]（Cy PNP =双（二环己基膦基甲基）吡咯），得到八面体低旋转氢化铁化合物[FeH（PMe 2 Ph）（N 2） （Cy PNP）]和[FeH（PMe 3）2（Cy PNP）]。这些新的氢化物以及先前报道的[FeMe（Cy PNP）]与硅烷反应形成一类新型的方形，中间自旋（S = 1）的甲硅烷基铁配合物[Fe（SiRPh 2）（Cy PNP）]（R = H，Me，F）。在空间上更易受到阻碍的氢化铁[FeH（t卜PNP）]（吨卜PNP =双（二-叔-butylphosphinomethyl）吡咯）也被用于分离的[Fe硅烷（SiH 2 PH）（吨卜PNP）]通过治疗PhSiH 3。[Fe（SiRPh 2）（Cy PNP）]在分子氮气氛下以低自旋[Fe（N 2）（SiRPh 2）（Cy PNP）]处于平衡状态，而[Fe（SiH 2 Ph）（t
• Investigation of Iron Silyl Complexes as Active Species in the Catalytic Hydrosilylation of Aldehydes and Ketones
  作者：C. Vance Thompson、Hadi D. Arman、Zachary J. Tonzetich

  DOI：10.1021/acs.organomet.1c00682

  日期：2022.2.28

  the hydrosilylation of aldehydes and ketones under mild conditions. The catalytic and stoichiometric reactivity of these complexes has been scrutinized in detail and found to support disparate pathways for hydrosilylation of aldehydes involving both a canonical Chalk–Harrod process and a peripheral pathway, which depends upon both precatalyst and substrate selection. Hydrosilylation of ketones, by

  [Fe(X)(L)( Cy PNP)] 类型的 Fe(II) 氢化物和甲硅烷基物质（X = H 或 SiR 3；L = N 2和/或 PMe 2 Ph；Cy PNP = 2 的阴离子， 5-之二(dicylcohexylphosphinomethyl)pyrrole) 用作在温和条​​件下醛和酮氢化硅烷化的活性催化剂。对这些配合物的催化和化学计量反应性进行了详细研究，发现它们支持醛的氢化硅烷化的不同途径，包括典型的 Chalk-Harrod 过程和外围途径，这取决于前催化剂和底物的选择。相比之下，酮的氢化硅烷化似乎通过涉及铁甲硅烷基物质和外围途径的共同机制进行。由这些研究产生的铁催化氢化硅烷化的独特机制框架与大多数先前提出的机制形成对比，后者的特点是仅将羰基插入到 Fe-H 键中。
• Catalytic asymmetric hydrosilylation of conjugated dienes: Effective control of regio- and enantioselectivities
  作者：Yasuo Hatanaka、Ken-ichi Goda、Futoshi Yamashita、Tamejiro Hiyama

  DOI：10.1016/0040-4039(94)80027-8

  日期：1994.10

  Hydrosilylation of (E)-1-phenyl-1,3-butadiene with HSiPhnX3−n (XCl, F; n = 1, 2) was catalyzed by palladium catalyst generated in situ from (η3-C3H5PdCl)2 and (R)-2-diphenylphosphino-1,1′-binaphthyl derivatives (2), giving optically active (Z)-1-phenyl-1-silyl-2-butenes (1) in good yields. The regio- and enantioselectivities of the reaction was found to be strongly affected by the structure of the

  的氢化硅烷化（ë）-1-苯基-1,3-丁二烯与HSiPh Ñ X 3- Ñ（XCl，F; Ñ = 1，2）通过从（原位产生钯催化剂催化η 3 -C 3 H 5 PdCl）2和（R）-2-二苯基膦基-1,1'-联萘基衍生物（2），以良好的产率得到旋光的（Z）-1-苯基-1-甲硅烷基-2-丁烯（1）。发现反应的区域选择性和对映选择性受氢化硅烷和膦配体的结构的强烈影响。
• Selective synthesis of halosilanes from hydrosilanes and utilization for organic synthesis
  作者：Atsutaka Kunai、Joji Ohshita

  DOI：10.1016/s0022-328x(03)00254-7

  日期：2003.11

  Selective synthesis of halosilanes has been examined. Various types of halosilanes and halohydrosilanes, such as R3SiX, R2SiHX, R2SiX2, RSiH2X, RSiHX2 (X = Cl, Br, F), were obtained by the reactions of the corresponding hydrosilanes with Cu(II)-based reagents selectively in high yields. This method could be also applied to the synthesis of chlorofluorosilanes and chlorohydrogermanes. On the other hand, iodo- and bromosilanes and germanes were obtained by Pd- or Ni-catalyzed hydride-halogen exchange reactions of hydrosilanes with alkyl or allyl halides. Their synthetic applications have been demonstrated by using iodo-and bromosilanes and chlorofluorosilanes. (C) 2003 Elsevier Science B.V. All rights reserved.