3-bromophenyl phenyl selenide | 856074-00-5

• 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: 3-bromophenyl phenyl selenide
• 英文别名: 1-Bromo-3-phenylselanylbenzene；1-bromo-3-phenylselanylbenzene
• CAS: 856074-00-5
• 化学式: C₁₂H₉BrSe
• 分子量: 312.067
• InChiKey: QFBLYAVARRTGNC-UHFFFAOYSA-N

物化性质

• 沸点：
  147-148 °C(Press: 1 Torr)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 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：
  0

反应信息

• 作为反应物：
  描述：

  3-bromophenyl phenyl selenide 在 copper diacetate 、 sodium acetate 、 calcium carbonate 作用下， 生成 Phenyl-(3-hydroxy-phenyl)-selenid
  参考文献：
  名称：

  Keimatsu; Yokota, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1931, vol. 51, p. 605,613; dtsch. Ref. S. 89, 91, 92

  摘要：

  DOI：
• 作为产物：
  描述：

  苯基溴化硒 、 3-溴苯硼酸 在 caesium carbonate 作用下， 以 PEG-400 为溶剂， 反应 8.0h， 以82%的产率得到3-bromophenyl phenyl selenide
  参考文献：
  名称：

  Magnetically Separable CuFe₂O₄Nanoparticle Catalyzed C–Se Cross Coupling in Reusable PEG Medium

  摘要：

  通过可磁分离的 CuFe2O4 纳米粒子催化有机硼烷与 PhSeBr 在可回收 PEG-400 介质中在 80 °C 和 Cs2CO3 为基础的反应，开发了一种简单有效的合成不对称二芳基硒化物的方法。使用该方案，以良好至优异的产率获得了多种不对称硒化物。铁氧体铜纳米粒子被磁分离、回收并重复使用最多四个周期。

  DOI：

  10.1246/cl.2012.585

文献信息

• CuS/Fe: a novel and highly efficient catalyst system for coupling reaction of aryl halides with diaryl diselenides
  作者：Yaming Li、Huifeng Wang、Xiaoying Li、Tao Chen、Defeng Zhao

  DOI：10.1016/j.tet.2010.09.061

  日期：2010.11

  The CuS catalyzed coupling reactions of aryl halides and diaryl diselenides were accelerated by the addition of Fe powder in only 3–12 h with good to excellent yields. SEM–EDX indicated that the in situ iron oxides as support against catalyst agglomeration accelerated the reaction. This catalyst system was also demonstrated recyclable without significant loss of catalytic activity.

  仅在3到12 h内加入铁粉即可加快CuS催化的芳基卤化物和二芳基二硒化物的偶联反应。SEM-EDX表明，原位氧化铁作为载体防止催化剂的团聚加速了反应。还证明了该催化剂体系是可回收的，而没有明显的催化活性损失。
• Trichloroisocyanuric Acid‐Promoted Synthesis of Arylselenides and Aryltellurides from Diorganyl Dichalcogenides and Arylboronic Acids at Ambient Temperature
  作者：Nan Sun、Kai Zheng、Pengyuan Sun、Yang Chen、Liqun Jin、Baoxiang Hu、Zhenlu Shen、Xinquan Hu

  DOI：10.1002/adsc.202100371

  日期：2021.7.20

  method for the synthesis of arylselenides and aryltellurides has been established based on the oxidative cross-coupling between diorganyl dichalcogenides and aryl boronic acids. With trichloroisocyanuric acid as an oxidant, the reaction proceeded smoothly to afford the desired products in 45–97% yields at ambient temperature. Three reaction reagents used in this method are stoichiometric and the oxidation

  基于二有机二硫属元素化物和芳基硼​​酸之间的氧化交叉偶联，建立了一种无过渡金属合成芳基硒化物和芳基碲化物的方法。以三氯异氰尿酸为氧化剂，反应顺利进行，在室温下以 45-97% 的产率得到所需产物。该方法中使用的三种反应试剂都是化学计量的，氧化副产物异氰脲酸可以很容易地分离和回收。除了芳基硼酸，芳基三氟硼酸盐和芳基三羟基硼酸盐也能够进行这种转化。
• Solvent-Controlled Halo-Selective Selenylation of Aryl Halides Catalyzed by Cu(II) Supported on Al₂O₃. A General Protocol for the Synthesis of Unsymmetrical Organo Mono- and Bis-Selenides
  作者：Tanmay Chatterjee、Brindaban C. Ranu

  DOI：10.1021/jo401062k

  日期：2013.7.19

  Alumina-supported Cu(II) efficiently catalyzes selenylation of aryl iodides and aryl bromides by diaryl, dialkyl, and diheteroaryl diselenides in water and PEG-600, respectively, leading to a general route toward synthesis of unsymmetrical diaryl, aryl–alkyl, aryl–heteroaryl, and diheteroaryl selenides. A sequential reaction of bromoiodobenzene with one diaryl/diheteroaryl/dialkyl diselenide in water and another

  氧化铝负载的Cu（II）分别在水和PEG-600中有效地催化二芳基，二烷基和二杂芳基二硒化物对芳基碘化物和芳基溴化物的硒化，从而通向合成不对称二芳基，芳基-烷基，芳基-杂芳基和二杂芳基硒化物。在第二步中，溴碘代苯与一种二芳基/二杂芳基/二烷基二硒化物和另一种二芳基/二杂芳基/二烷基二硒化物在水中的顺序反应在第二步中产生不对称的二芳基，二杂芳基或芳基-烷基双-硒基苯。通过该方案，可以高收率获得功能化的有机单硒化物和双硒化物的文库，包括一个有效的生物活性分子和一对生物活性硒化物的类似物。反应是化学选择性的和高产率的。铜铝2O 3催化剂可循环使用七次，而不会损失任何活性。
• Efficient Heterogeneous Copper-Catalysed C–Se Coupling of Aryl Iodides with Symmetrical Diselenides towards Unsymmetrical Monoselenides
  作者：Ruonan Zhao、Chenyu Yan、Yuanyuan Jiang、Mingzhong Cai

  DOI：10.3184/174751918x15409874473285

  日期：2018.11

  A highly efficient heterogeneous copper(I)-catalysed C–Se coupling of aryl iodides with diaryl diselenides was achieved in dimethylformamide at 110 °C under neutral conditions by using a 10 mol% of bipyridine-functionalised MCM-41-supported copper(I) complex [bpy-MCM-41-CuI] as the catalyst and magnesium as the reductive reagent, yielding a variety of unsymmetrical diaryl selenides in good to excellent

  通过使用 10 mol% 的联吡啶官能化 MCM-41 负载的铜 (I)，在二甲基甲酰胺中，在 110 °C 下，在中性条件下实现了芳基碘化物与二芳基二硒化物的高效异相铜 (I) 催化的 C-Se 偶联络合物 [bpy-MCM-41-CuI] 作为催化剂，镁作为还原剂，产生各种不对称的二芳基硒化物，产率良好至极好。这种非均相铜催化剂可以通过反应溶液的简单过滤很容易地回收并循环使用至少七次而不会显着损失活性。
• Solvent selective phenyl selenylation and phenyl tellurylation of aryl boronic acids catalyzed by Cu(II) grafted functionalized polystyrene
  作者：Susmita Roy、Tanmay Chatterjee、Sk. Manirul Islam

  DOI：10.1016/j.tetlet.2014.12.055

  日期：2015.2

  A solvent-selective methodology for the phenyl selenylation and phenyl tellurylation of aryl boronic acids has been developed for the first time using a polymer supported Cu(II) catalyst. The catalyst was synthesized by anchoring Cu(OAc)(2) onto a functionalized polystyrene with pyridine thiosemicarbazone ligand. It was then characterized properly by SEM, EDAX, FT-IR, TGA, and EPR experiments. The catalyst smoothly catalyzes phenyl selenylation of aryl boronic acids in water and phenyl tellurylation of aryl boronic acids in PEG-600, selectively. Thus a wide variety of unsymmetrical organodiaryl or aryl-heteroaryl selenides and tellurides have been synthesized by this protocol. The catalyst was recycled up to six runs without any appreciable loss of catalytic activity. (C) 2014 Elsevier Ltd. All rights reserved.