(E)-(1,2-difluoro-1,2-ethenediyl)bis(tributylstannane)

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机过渡后金属化合物
• 英文名称: (E)-(1,2-difluoro-1,2-ethenediyl)bis(tributylstannane)
• 化学式: C₂₆H₅₄F₂Sn₂
• 分子量: 642.132
• InChiKey: JXIYHDPDUDTOOF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.91
• 重原子数：
  30
• 可旋转键数：
  20
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  邻碘溴苯 、 (E)-(1,2-difluoro-1,2-ethenediyl)bis(tributylstannane) 在 copper(l) iodide 、 四(三苯基膦)钯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 以62%的产率得到(E)-(1,2-difluoro-1,2-ethendiyl)-bis-[2'-bromobenzene]
  参考文献：
  名称：

  Stereoselective Preparation of (E)-(1,2-Difluoro-1,2-ethenediyl) Bis[tributylstannane] and Stereospecific Synthesis of (E)-1,2-Difluorostilbenes

  摘要：

  [GRAPHIC]The novel bisstannane (E)-(1,2-difluoro-1,2-ethenediyl) bis[tributylstannane] 2 was stereoselectively prepared in a high overall yield through a sequential synthetic route from chlorotrifluoroethylene 1. The synthetic application of this novel bisstannane 2 was exemplified in the Pd(PPh3)(4)/Cul-catalyzed cross-coupling reactions with aryl iodides, yielding (E)-1,2-difluorostilbenes 3 in moderate to high yields.

  DOI：

  10.1021/ol025686+

文献信息

• Stereospecific preparation of (1E,3E,5E)-3.4-difluoro-1,6-diphenylhexatriene and (2E,4E,6E)-diethyl-4,5-difluoroocta-2,4,6-trienedioate
  作者：Qibo Liu、Dale C. Swenson、Donald J. Burton

  DOI：10.1016/j.jfluchem.2010.12.008

  日期：2011.2

  (E/Z = 89/11) with (E)-(1,2-difluoro-1,2-ethenediyl)bis[tributylstannane], 1, in DMF at room temperature stereospecifically gave only (1E,3E,5E)-3,4-difluoro-1,6-diphenylhexatriene. Similarly, palladium(0) catalyzed coupling of (E)-ethyl 3-bromoacrylate as the vinyl halide precursor stereospecifically gave (2E,4E,6E)-diethyl-4,5-difluoroocta-2,4,6-trienedioate. This work demonstrates that a non-fluorine-containing

  在室温下，DMF中钯（0）在DMF中催化β-溴苯乙烯（E / Z  = 89/11）与（E）-（1,2-二氟-1,2-乙炔基）双[三丁基锡烷] 1的偶联仅给出（1 E，3 E，5 E）-3,4-二氟-1,6-二苯基己三烯。类似地，钯（0）催化的（E）-3-溴丙烯酸乙酯（作为卤化乙烯基酯前体）的立体定向偶合得到（2 E，4 E，6 E）-二乙基-4,5-二氟辛基-2,4,6-三烯二酸酯。这项工作表明，不含氟的乙烯基溴将选择性地与1偶联。并能够实现立体定向的混合多烯体系的制备。的（ë） -乙基3- bromoacrylate与耦合1示出了混合官能己三烯系统可以很容易地访问通过这一方法。（2 E，4 E，6 E）-二乙基-4,5-二氟辛基-2,4,6-三烯二酸酯的X射线结构证实了其结构。
• The stereoselective synthesis of (E)-octafluoro-1,3,5-hexatriene and (3E,5E,7E)-dodecafluoro-1,3,5,7,9-decapentaene
  作者：Qibo Liu、Donald J. Burton

  DOI：10.1016/j.jfluchem.2009.07.009

  日期：2009.10

  (E)-(1,2-Difluoro-1,2-ethenediyl)bis[tributylstannane], 3, readily undergoes a Pd(PPh3)(4)/Cul-catalyzed cross-coupling reaction with iodotrifluoroethene to yield (E)-octafluoro-1,3,5-hexatriene, 4, in high isomeric purity. (1Z,3E,5Z)-(1,2,3,4,5,6-Hexafluoro-1,3,5-hexenetriyl)bis[tributylstannane], 7, was sequentially prepared from (1Z,3E,5Z)-(1,2,3,4,5,6-hexafluoro-1,3,5-hexenetriyl)bis[triethylsilane], 5, which was prepared via a Pd(PPh3)(4)/Cul-catalyzed cross-coupling reaction of 3 with (E)-1,2-difluoro-1-iodo-2-triethylsilylethene, 6. Pd(PPh3)(4)/Cul cross-coupling of 7 with iodotrifluoroethene gave (3E,5E,7E)-dodecafluoro-1,3,5,7,9-decapentacne, 8. (C) 2009 Elsevier B.V. All rights reserved.

  (E)-(1,2-二氟乙二烯基)二二丁基ictionary，3会通过 Pd(PPh3)(4)/Cul催化的双 allen 酯反应与碘三氟乙烷发生反应，生成(E)-八氟甲基-1,3,5-三烯六烷基复合物，4在高度单一构选纯度下。若将(1Z,3E,5Z)-(1,2,3,4,5,6-六氟-1,3,5-三烯)二ictionary，7从(1Z,3E,5Z)-(1,2,3,4,5,6-六氟-1,3,5-三烯)二三乙基胺ivate，5经 Pd(PPh3)(4)/Cul催化的双 allen 酯反应生成——这里5是将3与(E)-1,2-二氟-1-碘的-2-三乙基硅ylethane发生反应所得。接着，将7与碘三氟乙烷进行 Pd催化的双 allen 酯反应，得到(3E,5E,7E)-十二氟-1,3,5,7,9-五庚烷基多戊二烯，8。2009年，Elsevier B.V. 版权所有。
• Sparkling Organic Phosphorescence from Fluorinated Tetrathia[7]helicenes: Synthesis and Photophysical, Electrochemical and Computational Studies
  作者：Alberto Bossi、Patrizia R. Mussini、Gianluca Farinola、Marta Penconi、Silvia Cauteruccio、Mark E. Thompson、Emanuela Licandro

  DOI：10.1002/chem.202300339

  日期：——

  Putting a green spin on [7]TH: Fluorination of the tetrathia[7]helicene backbone disclosed important functionalization-related structure-electronic alterations crucial in the design of novel chiral derivatives. [7]THs also show brilliant green phosphorescence resulting from enhanced spin-orbit coupling (SOC) due to an S-atom effect and distortion annulation.

  在 [7]TH 上进行绿色旋转：四硫[7]螺旋烯主链的氟化揭示了重要的功能化相关结构电子改变，这对新型手性衍生物的设计至关重要。[7]THs 还显示出明亮的绿色磷光，这是由于 S 原子效应和畸变环化而增强的自旋轨道耦合 (SOC)。
• (1<i>E</i>,3<i>E</i>,5<i>E</i>)-1,2,3,4,5,6-Hexafluoro-1,6-diphenylhexatriene
  作者：Dale C. Swenson、Xiaobang Gao、Donald J. Burton

  DOI：10.1107/s0108270100007502

  日期：2000.8.15

  The title triene, C18H10F6, was prepared via the Pd-0 coupling reaction of (E)-(1,2-difluoro-1,2-ethenediyl)bis(tributylstannane) with (Z)-beta-iodo-alpha,beta-difluorostyrene in N,N'-dimethylformamide/tetrahydrofuran. The crystal structure shows the product to be the 1E,3E,5E isomer. Due to steric interactions between F atoms, the double bonds are not coplanar. The planes defined by the two terminal double bonds are almost perpendicular.
• Stereoselective Preparation of (<i>E</i>)-(1,2-Difluoro-1,2-ethenediyl) Bis[tributylstannane] and Stereospecific Synthesis of (<i>E</i>)-1,2-Difluorostilbenes
  作者：Qibo Liu、Donald J. Burton

  DOI：10.1021/ol025686+

  日期：2002.5.1

  [GRAPHIC]The novel bisstannane (E)-(1,2-difluoro-1,2-ethenediyl) bis[tributylstannane] 2 was stereoselectively prepared in a high overall yield through a sequential synthetic route from chlorotrifluoroethylene 1. The synthetic application of this novel bisstannane 2 was exemplified in the Pd(PPh3)(4)/Cul-catalyzed cross-coupling reactions with aryl iodides, yielding (E)-1,2-difluorostilbenes 3 in moderate to high yields.