4,4''-difluoro-1,1':4',1''-terphenyl

• 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: 4,4''-difluoro-1,1':4',1''-terphenyl
• 英文别名: 4,4''-Difluoro-1,1',4',1''-terphenyl；1,4-bis(4-fluorophenyl)benzene
• 化学式: C₁₈H₁₂F₂
• 分子量: 266.29
• InChiKey: HLSJIXGPDHPFPG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• 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：
  2

反应信息

• 作为产物：
  描述：

  对苯二酚 在 palladium diacetate 、 三乙胺 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 2.0h， 生成 4,4''-difluoro-1,1':4',1''-terphenyl
  参考文献：
  名称：

  Palladium-Catalyzed, Ligand-Free Suzuki Reaction in Water Using Aryl Fluorosulfates

  摘要：

  Aryl fluorosulfates were prepared by a simple method and employed as coupling partners in the Suzuki-Miyaura reaction. The cross-coupling reactions were performed in water under air at room temperature without ligands or additives such as surfactants or phase-transfer reagents and proceeded smoothly to give excellent yields. Aryl fluorosulfates could also be used as alternatives to halides or triflates in other coupling reactions.

  DOI：

  10.1021/acs.orglett.5b00654

文献信息

• Sterically hindered N-aryl/benzyl substituted piperidoimidazolin-2-ylidene palladium complexes and their catalytic activities
  作者：Elif Gacal、Serpil Denizaltı、Armağan Kınal、Aytaç Gürhan Gökçe、Hayati Türkmen

  DOI：10.1016/j.tet.2018.10.003

  日期：2018.11

  cross coupling. The N-aryl substituted complex 3b was a highly efficient precatalyst and successfully employed in Suzuki-Miyaura cross coupling reactions of (hetero)aryl chlorides with arylboronic acids in air. In addition, the oxidative addition step of the reaction mechanism involving chlorobenzene and the catalysts 3a, 3b, 3c and 3d were computationally investigated by the DFT-ω-B97X-D method and

  制备了一系列的N-芳基（2a，b）或苄基（2c，d）取代的哌啶并咪唑啉盐及其钯配合物（3a - d），并通过1 H，13 C NMR，IR光谱和元素分析进行​​了表征。3a和3c的晶体结构已经通过X射线晶体学确定。热重分析（TGA）用于复合物（3a – d）。钯配合物已被用作铃木-宫浦交叉偶联的催化剂。N-芳基取代的配合物3b是一种高效的预催化剂，已成功用于空气中（杂）芳基氯与芳基硼酸的Suzuki-Miyaura交叉偶联反应。此外，通过DFT-计算方法研究了涉及氯苯与催化剂3a，3b，3c和3d的反应机理的氧化加成步骤。ω-B97X-D法与催化结果完全吻合。为了测量新配体的σ-给体和π-受体性质，还制备了羰基铑配合物。
• Zwitterionic Palladium Complexes: Room-Temperature Suzuki–Miyaura Cross-Coupling of Sterically Hindered Substrates in an Aqueous Medium
  作者：Jhen-Yi Lee、Dabalina Ghosh、Jing-Yi Lee、Shih-Sheng Wu、Ching-Han Hu、Shuang-De Liu、Hon Man Lee

  DOI：10.1021/om500834y

  日期：2014.11.24

  charge on the ligand ancillary. The pyridine ligand in the zwitterionic complexes can be facilely replaced by phosphine ligands. Seven of these new complexes were successfully characterized by X-ray crystallography. The zwitterionic phosphine complexes were highly efficient in catalyzing room-temperature Suzuki–Miyaura reactions between sterically hindered aryl chlorides and arylboronic acids in an aqueous

  从氯丙酮和咪唑衍生物之间的反应直接制备了一系列新的咪唑氯化物。吡啶使这些盐中酮基旁边的亚甲基质子脱质子化，导致形成与钯配位的单齿配体，容易形成两性离子阴离子钯吡啶配合物，在配体辅助上带有正式的正电荷。两性离子络合物中的吡啶配体可以容易地被膦配体取代。这些新的配合物中的七个已通过X射线晶体学成功表征。两性离子膦配合物在水性介质中催化空间受阻芳基氯和芳基硼酸之间的室温Suzuki-Miyaura反应方面非常有效。
• Recyclable and Reusable Pd(OAc)₂/DABCO/PEG-400 System for Suzuki−Miyaura Cross-Coupling Reaction
  作者：Jin-Heng Li、Wen-Jie Liu、Ye-Xiang Xie

  DOI：10.1021/jo050353m

  日期：2005.7.1

  A stable and efficient Pd(OAc)2/DABCO (triethylenediamine) catalytic system for Suzuki−Miyaura cross-coupling reaction has been developed. In the presence of Pd(OAc)2 and DABCO, coupling of aryl halides with arylboronic acids was carried out smoothly to afford good to excellent yields and high turnover numbers (TONs) (the maximal TONs were up to 960 000 for the reaction of 1-iodo-4-nitrobenzene with

  已开发出稳定有效的Sduki-Miyaura交叉偶联反应的Pd（OAc）2 / DABCO（三亚乙基二胺）催化体系。在Pd（OAc）2和DABCO存在下，芳基卤化物与芳基硼酸的偶联反应顺利进行，以提供良好至优异的收率和高周转率（TONs）（1反应1时最大TONs高达960 000） -异碘-4-硝基苯与苯基硼酸），使用PEG-400作为溶剂。此外，Pd（OAc）2 / DABCO / PEG-400系统可以循环使用五次，而对芳基碘化物和溴化物的催化活性没有任何损失。
• Thieme Journal Awardees - Where Are They Now? On Cobalt-Catalyzed Biaryl Coupling Reactions
  作者：Axel Jacobi von Wangelin、Matthias Mayer、Waldemar Czaplik

  DOI：10.1055/s-0029-1218013

  日期：2009.11

  An operationally simple biaryl coupling reaction has been developed. The underlying domino process involves in situ Grignard formation from aryl bromides and subsequent homocoupling with catalytic CoCl 2 and I bar synthetic air as terminal oxidant.

  已开发出操作简单的联芳基偶联反应。潜在的多米诺骨牌过程涉及由芳基溴化物原位形成格氏，随后与催化 CoCl 2 和 I bar 合成空气作为末端氧化剂均偶联。
• Synthesis of symmetrical terphenyl derivatives by PdCl₂-catalyzed Suzuki–Miyaura reaction of dibromobenzene using 3-(diphenylphosphino)propanoic acid as a ligand
  作者：Ningning Gu、Yashuai Liu、Ping Liu、Xiaowei Ma、Yan Liu

  DOI：10.1080/00397911.2015.1126606

  日期：2016.1.17

  ABSTRACT A simple and efficient catalytic system for PdCl2 catalyzing the Suzuki–Miyaura reaction of dibromobenzene and arylboronic acid has been developed by using 3-(diphenylphosphino)propanoic acid as a ligand in dimethylsulfoxide at 100 °C. Using this method, a series of symmetrical terphenyl derivatives were obtained with remarkably good yields, up to 93%. GRAPHICAL ABSTRACT

  摘要 利用 3-（二苯基膦基）丙酸作为二甲基亚砜中的配体，在 100 °C 下开发了一种简单有效的 PdCl2 催化体系，用于催化二溴苯和芳基硼酸的 Suzuki-Miyaura 反应。使用这种方法，以非常好的收率获得了一系列对称的三联苯衍生物，高达 93%。图形概要