1-fluoro-4-λ¹-selanylbenzene,tributyltin | 206431-87-0

• 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: 1-fluoro-4-λ¹-selanylbenzene,tributyltin
• 英文别名: (4-fluorophenyl)selenotributylstannane；4-fluorophenylselenotributylstannane；tributyltin 4-fluorophenyl selenide；4-FC6H4SeSnBu3
• CAS: 206431-87-0
• 化学式: C₁₈H₃₁FSeSn
• 分子量: 464.113
• InChiKey: ZUMPVUWHEYOZKK-UHFFFAOYSA-M

物化性质

• 沸点：
  409.8±47.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  21.0
• 可旋转键数：
  11.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为反应物：
  描述：

  1-fluoro-4-λ¹-selanylbenzene,tributyltin 在 [Cu2(μ-I)2(1,10-phenanthroline)2] 作用下， 以 N,N-二甲基乙酰胺 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.33h， 生成 [1,8-bis(4-fluorophenylselenomethyl)anthracenyl]palladium(II) chloride
  参考文献：
  名称：

  “无磷” Mizoroki–Heck和Suzuki–Miyaura反应中的钯缓释预催化剂和纳米颗粒

  摘要：

  AbstractThe Mizoroki–Heck reaction of electron‐rich aryl iodides was studied using a phosphine‐free catalytic system with a broad range of pre‐catalysts of varied stability and structure based on organoselenium chelators. The application of the “mercury test” by observing the response of the catalytic systems studied not only to the addition, but also to the withdrawal of Hg allowed us to establish a critical role of nanoparticles in the operation of the phosphine‐free catalytic systems. A three‐stage mechanistic scheme involving a slow stage served by mononuclear Pd species, and the main fast stage served by Pd nanoparticles, and terminated by the nanoparticle decay is proposed as a general mechanistic paradigm for the phosphine‐free Mizoroki–Heck and the related Suzuki–Miyaura reactions.magnified image

  DOI：

  10.1002/adsc.201400562
• 作为产物：
  描述：

  4-Fluorselenoanisol 、 三正丁基氢锡 、 phenyl tributylstannyl selenide 在 AIBN 作用下， 以 苯 为溶剂， 生成 1-fluoro-4-λ¹-selanylbenzene,tributyltin
  参考文献：
  名称：

  芳基碲化物与三丁基锡烷基，三丁基锗烷基和三（三甲基甲硅烷基）甲硅烷基的自由基反应的可逆性

  摘要：

  1个H，13 C，29的Si，77硒，119 Sn和125个碲NMR波谱表明，甲基，伯和仲烷基，通过aryltelluroalkanes（的反应所产生的4 - 9）与三丁基锡氢化物，tributylgermanium氢化物或三（三甲基甲硅烷基）硅烷）标准自由基条件（苯，AIBN）下是能够置换三丁基锡烷基，tributylgermyl和三（三甲基硅基）从aryltellurotributylstannanes（甲硅烷基的1，2），aryltellurotributylgermanes（10，11）和aryltellurotris（三甲硅基）硅烷（13，14）。这些观察结果与高级从头算分子轨道研究一致。使用（化合价）双计算ζ补充有偏振功能，并与包含电子相关（MP2 / DZP）的赝基组预测甲锡烷基的位移（SNH能量壁垒3），甲锗烷基烷（GeH 3）和trisilylsilyl（（ ħ 3 Si

  DOI：

  10.1016/s0022-328x(97)00491-9

文献信息

• A Novel Route to the Synthesis of α-Arylselenosubstituted Carbonyl Compounds and Nitriles
  作者：Irina Beletskaya、Alexander Sigeev、Alexander Peregudov、Pavel Petrovskii

  DOI：10.1246/cl.2005.1348

  日期：2005.10

  Activated alkyl halides such as α-halocarbonyl compounds and α-halonitriles easily react with tributyltin arylselenides both in fluoride-mediated reaction and without any additives. The former protocol gives correspondingselenides under the mild conditions in near quantitative yields.

  α-卤代羰基化合物和 α-卤腈等活性烷基卤化物在氟化物介导的反应中很容易与三丁基锡芳基硒化物反应，无需任何添加剂。前一个方案在温和的条件下以接近定量的产率给出相应的硒化物。
• Copper(I)-catalyzed arylselenylation of aryl bromides and iodides
  作者：Irina P Beletskaya、Alexander S Sigeev、Alexander S Peregudov、Pavel V Petrovskii

  DOI：10.1016/s0040-4039(03)01756-8

  日期：2003.9

  A new protocol to prepare unsymmetrical diarylselenides using the reaction of aryl bromides and iodides with easily available Bu3SnSeAr catalyzed by Cu(I) complexes under rather mild conditions and with a very high yield is described.

  描述了一种使用芳基溴化物和碘化物与Cu（I）络合物在相当温和的条件下催化的，易得的Bu 3 SnSeAr的反应，在相当温和的条件下以非常高的收率制备不对称二芳基硒化物的新方案。
• Microwave-assisted Synthesis of Diaryl Selenides. Elucidation of Cu(I)-catalyzed Reaction Mechanism
  作者：Irina P. Beletskaya、Alexander S. Sigeev、Alexander S. Peregudov、Pavel V. Petrovskii、Victor N. Khrustalev

  DOI：10.1246/cl.2010.720

  日期：2010.7.5

  A novel microwave-assisted cross-coupling of trialkyltin arylselenides 1 with arylbromides using [(phen)CuI]2 afforded unsymmetrical diarylselenides 3 in high to excellent yields. A plausible catalytic cycle for Cu(I)-catalysed cross-coupling has been proposed. A key intermediate in this catalytic cycle was synthesized and its structure was determined by X-ray diffractometry.

  利用[(phen)CuI]2，在新型微波辅助下将三烷基锡芳基硒化物 1 与芳基溴化物进行交叉偶联，得到了不对称的二芳基硒化物 3，收率高至极佳。提出了一种 Cu(I)催化交叉偶联的合理催化循环。我们合成了该催化循环中的一个关键中间体，并通过 X 射线衍射测定法确定了其结构。
• ——
  作者：I. P. Beletskaya、A. S. Sigeev、A. S. Peregudov、P. V. Petrovskii

  DOI：10.1023/a:1013460213633

  日期：——

  Tributyltin aryl selenides are highly efficient arylselenating agents in reactions with aryl iodides and aryl triflates under catalysis with Pd and Ni complexes respectively. They also may be used as efficient source of active arylselenolate anion in the presence of fluoride ions in reaction of arylselenation of alkyl halides and activated aryl fluorides.
• ——
  作者：I. P. Beletskaya、A. S. Sigeev、A. S. Peregudov、P. V. Petrovskii

  DOI：10.1023/a:1013913816069

  日期：——

  Tributyltin aryl selenides are convenient and highly efficient arylselenating agents in reactions with acyl chlorides. The activity of acetic anhydride is considerably lower but it can be involved into the arylselenation reaction in the presence of PdCl2(PPh3)(2) or boron trifluoride etherate as catalysts.