1-氯-3-(4-氟苯基)苯 | 80254-79-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1-氯-3-(4-氟苯基)苯
• 英文名称: 3-chloro-4'-fluoro-1,1'-biphenyl
• 英文别名: 3-chloro-4'-fluorobiphenyl；3-Chlor-4'-fluorbiphenyl；1,1'-Biphenyl, 3-chloro-4'-fluoro-；1-chloro-3-(4-fluorophenyl)benzene
• CAS: 80254-79-1
• 化学式: C₁₂H₈ClF
• 分子量: 206.647
• InChiKey: WCKTVTBPFMCTRT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  14
• 可旋转键数：
  1
• 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：

  2-甲氧基苯基硼酸 、 1-氯-3-(4-氟苯基)苯 在 palladium diacetate 2-双环己基膦-2',6'-二甲氧基联苯 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 21.0h， 生成 4-fluoro-2''-methoxy-[1,1';3',1'']terphenyl
  参考文献：
  名称：

  A Practical and General Synthesis of Unsymmetrical Terphenyls

  摘要：

  [GRAPHICS]A synthetic procedure was developed that enables sequential chemoselective Suzuki-Miyaura cross-coupling of chlorobromobenzene with arylboronic acids. The first coupling is achieved at room temperature using a ligandless palladium catalyst. The chlorobiaryl product can then be subjected directly to the second coupling, facilitated by the SPhos ligand. Using this methodology, parallel synthesis of 32 unsymmetrical o-, m-, and p-terphenyl compounds was accomplished in good to excellent overall yields.

  DOI：

  10.1021/jo701308b
• 作为产物：
  描述：

  间氯溴苯 、 4-氟苯硼酸 在 palladium diacetate potassium phosphate 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 1-氯-3-(4-氟苯基)苯
  参考文献：
  名称：

  A Practical and General Synthesis of Unsymmetrical Terphenyls

  摘要：

  [GRAPHICS]A synthetic procedure was developed that enables sequential chemoselective Suzuki-Miyaura cross-coupling of chlorobromobenzene with arylboronic acids. The first coupling is achieved at room temperature using a ligandless palladium catalyst. The chlorobiaryl product can then be subjected directly to the second coupling, facilitated by the SPhos ligand. Using this methodology, parallel synthesis of 32 unsymmetrical o-, m-, and p-terphenyl compounds was accomplished in good to excellent overall yields.

  DOI：

  10.1021/jo701308b

文献信息

• Aerobic ligand-free Suzuki coupling catalyzed by in situ-generated palladium nanoparticles in water
  作者：Debasree Saha、Kalicharan Chattopadhyay、Brindaban C. Ranu

  DOI：10.1016/j.tetlet.2008.12.063

  日期：2009.3

  efficient procedure for Suzuki coupling of aryl bromides/iodides with aryl- and alkylboronic acids catalyzed by in situ-generated palladium(0) nanoparticles in water without any ligand in open air to produce a variety of functionalized biaryls and alkyl-aryls has been developed. The boronic acids act here as the reducing agent for the formation of Pd nanoparticles. The reactions are remarkably fast (5 min)

  一种简单有效的方法，用于将芳基溴化物/碘化物与原位生成的钯（0）纳米粒子在水中无任何配体的情况下，在露天条件下催化的芳基溴化物/碘化物与芳基和烷基硼酸偶合，具有多种官能化的联芳基和烷基芳基已开发。硼酸在这里用作Pd纳米颗粒形成的还原剂。反应非常快（5分钟），产率高。该催化剂最多可循环运行三次，而不会降低效率。
• Aminoborylation/Suzuki–Miyaura tandem cross coupling of aryl iodides as efficient and selective synthesis of unsymmetrical biaryls
  作者：Ludovic Marciasini、Nicolas Richy、Michel Vaultier、Mathieu Pucheault

  DOI：10.1039/c1cc14605j

  日期：——

  Sequential borylation of a first aryl iodide using a dialkylaminoborane followed by a Suzuki-Miyaura cross coupling of second aryl iodide ended up with an efficient, selective and practical synthesis of unsymmetrical biaryls. This tandem coupling shows a wide range of applicability.

  使用二烷基氨基硼烷对第一芳基碘进行顺序硼化，然后对第二芳基碘进行Suzuki-Miyaura交叉偶联，最终实现了不对称联芳基的高效，选择性和实用合成。这种串联联接器显示出广泛的适用性。
• Visible-Light-Promoted, Catalyst-Free Gomberg–Bachmann Reaction: Synthesis of Biaryls
  作者：Juyoung Lee、Boseok Hong、Anna Lee

  DOI：10.1021/acs.joc.9b00557

  日期：2019.7.19

  Biaryls were synthesized via a novel visible-light-promoted Gomberg–Bachmann reaction that does not require a photosensitizer or any metal reagents. The formation of an electron donor–acceptor complex between aryl diazonium salts and pyridine allows, under visible-light irradiation, the synthesis of biaryls in moderate-to-high yields.

  联芳基是通过不需要光敏剂或任何金属试剂的新型可见光促进的Gomberg-Bachmann反应合成的。在芳基重氮盐和吡啶之间形成电子供体-受体配合物，可以在可见光照射下以中等至高收率合成联芳基。
• Iron-catalyzed oxidative coupling of arylboronic acids with benzene derivatives through homolytic aromatic substitution
  作者：Nanase Uchiyama、Eiji Shirakawa、Ryo Nishikawa、Tamio Hayashi

  DOI：10.1039/c1cc14694g

  日期：——

  Fe(OTf)(3)-1,10-phenanthroline catalyzes oxidative coupling of arylboronic acids with benzene derivatives using t-BuOOt-Bu as an oxidant. The reaction proceeds through homolytic aromatic substitution with aryl radicals generated from arylboronic acids and t-BuO .

  Fe（OTf）（3）-1,10-菲咯啉使用t-BuOOt-Bu作为氧化剂催化芳基硼酸与苯衍生物的氧化偶联。该反应通过用芳基硼酸和t-BuO产生的芳基进行均相芳族取代而进行。
• Metal-catalyzed chemical activation of calcium carbide: New way to hierarchical metal/alloy-on-carbon catalysts
  作者：Andrey N. Lebedev、Konstantin S. Rodygin、Roman M. Mironenko、Elina R. Saybulina、Valentine P. Ananikov

  DOI：10.1016/j.jcat.2022.01.034

  日期：2022.3

  before the reaction led to the alloys, and the ratio of the salts simply determined the ratio of the metals in the desired alloy. This approach allowed the synthesis of highly active metals/alloys on carbon catalysts with intrinsic hierarchical organization, which ensures a long-life cycle in the reaction. The obtained catalysts were successfully tested in the Suzuki-Miyaura cross-coupling reaction and showed

  开发了一种简单有效的合成“金属/合金-碳”催化剂的策略。在 700°C 的氯气气流中进行电石分解后，获得了一种高度有序的超纯石墨状碳材料作为催化剂载体。当在分解之前将 Pd、Pt、Ag、Au、Co、Ni、Fe、Cu 盐添加到电石中时，尽管存在氧化气氛，但金属会被元素碳从盐中还原。金属颗粒在层状碳材料的表面形成，覆盖着一层薄薄的高纯度碳并部分浸入其中。由于碳的多孔结构，催化活性的剩余金属可用于有机分子。同时，金属牢牢地固定在碳壳内，在反应过程中和洗涤程序后不会被洗掉，在几个循环中保持其催化活性不变。在反应产生合金之前将各种盐混合在一起，盐的比例简单地确定了所需合金中金属的比例。这种方法允许在具有内在分层组织的碳催化剂上合成高活性金属/合金，从而确保反应的长生命周期。所获得的催化剂在 Suzuki-Miyaura 交叉偶联反应中成功进行了测试，并显示出优异的稳定性，几个循环的产率变化小于 1%（相比之下，商业催化剂的产率下降了