1,2,4,5-四氟-3-(4-甲基苯基)-6-(三氟甲基)苯 | 920264-42-2

• 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: 1,2,4,5-四氟-3-(4-甲基苯基)-6-(三氟甲基)苯
• 英文名称: 2,3,5,6-tetrafluoro-4'-methyl-4-(trifluoromethyl)-1,1'-biphenyl
• 英文别名: 2,3,5,6-tetrafluoro-4’-methyl-4-(trifluoromethyl)-1,1’-biphenyl；2,3,5,6-Tetrafluoro-4'-methyl-4-(trifluoromethyl)-1,1'-biphenyl；1,2,4,5-tetrafluoro-3-(4-methylphenyl)-6-(trifluoromethyl)benzene
• CAS: 920264-42-2
• 化学式: C₁₄H₇F₇
• 分子量: 308.198
• InChiKey: NIQCMZUDQFZPMY-UHFFFAOYSA-N

物化性质

• 沸点：
  256.8±35.0 °C(Predicted)
• 密度：
  1.392±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  八氟甲苯 、 对甲苯基溴化镁 在 Ni₂(i-Pr₂Im)4(COD) 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以26%的产率得到1,2,4,5-四氟-3-(4-甲基苯基)-6-(三氟甲基)苯
  参考文献：
  名称：

  Catalytic C−C Bond Formation Accomplished by Selective C−F Activation of Perfluorinated Arenes

  摘要：

  The first example of a catalytically active system for Suzuki-type cross-coupling reactions of perfluorinated arenes such as octafluorotoluene and decafluorobiphenyl is presented.

  DOI：

  10.1021/ja064068b

文献信息

• Palladium-Catalyzed Zinc-Amide-Mediated CH Arylation of Fluoroarenes and Heteroarenes with Aryl Sulfides
  作者：Shinya Otsuka、Hideki Yorimitsu、Atsuhiro Osuka

  DOI：10.1002/chem.201502101

  日期：2015.10.12

  heteroarenes with aryl sulfides proceeds smoothly with the aid of a palladium–N‐heterocyclic carbene catalyst. A bulky zinc amide, TMPZnCl⋅LiCl, plays a key role as an effective base to generate the corresponding arylzinc species in situ. This arylation protocol is practically much easier to perform than our previous method, which necessitates preparation of the arylzinc reagents in advance from the corresponding

  Ç  polyfluoroarenes和杂芳烃的与芳基硫化物ħ芳基化用钯- N-杂环卡宾催化剂的帮助下顺利进行。甲笨重锌酰胺，TMPZnCl ⋅的LiCl，起着以原位产生相应的芳基锌物种的有效碱关键作用。该芳基化方案实际上比我们以前的方法更容易执行，后者需要从相应的芳基卤化物预先制备芳基锌试剂。通过硫特异性反应（如S N Ar磺酰化反应和扩展的Pummerer反应）制备的芳基硫化物会经历这种直接芳基化，从而提供有趣的转化，而这些转化是传统的基于卤素的有机合成难以实现的。
• A General Direct Arylation of Polyfluoroarenes with Heteroaryl and Aryl Chlorides Catalyzed by Palladium Indolylphosphine Complexes
  作者：On Ying Yuen、Mueangkaew Charoensak、Chau Ming So、Chutima Kuhakarn、Fuk Yee Kwong

  DOI：10.1002/asia.201500048

  日期：2015.4

  The first general examples of direct coupling of heteroaryl chlorides, especially substituted 2‐pyridyl chlorides which were previously found to be problematic, with electron‐deficient polyfluoroarenes are reported. Pd(OAc)2 associated with 3‐(dicyclohexylphosphino)‐2‐phenylindole L1 serves as the effective catalyst which allows the challenging direct coupling of heteroaryl chlorides and polyfluoroarenes

  报道了杂芳基氯，特别是取代的2-吡啶基氯与先前的有电子缺陷的多氟芳烃直接偶联的第一个一般实例。与3-（二环己基膦基）-2-苯基吲哚L1缔合的Pd（OAc）2是有效的催化剂，可实现具有挑战性的杂芳基氯化物和多氟芳烃的直接偶联。除杂环外，在该催化剂体系下还可以使用多种非活化和活化的芳基氯化物和链烯基氯化物。可以实现低至1 mol％Pd的催化剂负载量。
• Dual Photoredox-/Palladium-Catalyzed Cross-Electrophile Couplings of Polyfluoroarenes with Aryl Halides and Triflates
  作者：Jian Qin、Shengqing Zhu、Lingling Chu

  DOI：10.1021/acs.organomet.0c00813

  日期：2021.7.26

  arylation of polyfluoroarenes with aryl halides and triflates in the presence of dialkylamines is reported for the first time. This synergistic protocol affords access to a series of fluorodiaryls from easily available starting materials under mild and operationally simple conditions. A series of mechanistic experiments, including the stoichiometric reactions of a ligated (aryl)Pd complex, Stern–Volmer fluorescence

  首次报道了在二烷基胺存在下，可见光光氧化还原/Pd 催化的多氟芳烃与芳基卤化物和三氟甲磺酸酯的交叉亲电芳基化。这种协同方案提供了在温和且操作简单的条件下从容易获得的起始材料中获得一系列氟二芳基化合物的途径。进行了一系列机械实验，包括连接（芳基）Pd 络合物的化学计量反应、Stern-Volmer 荧光猝灭研究、循环伏安法研究和紫外-可见光谱，以阐明该协同过程中的潜在催化途径。
• NHC Nickel-Catalyzed Suzuki–Miyaura Cross-Coupling Reactions of Aryl Boronate Esters with Perfluorobenzenes
  作者：Jing Zhou、Johannes H. J. Berthel、Maximilian W. Kuntze-Fechner、Alexandra Friedrich、Todd B. Marder、Udo Radius

  DOI：10.1021/acs.joc.6b01041

  日期：2016.7.1

  An efficient Suzuki–Miyaura cross-coupling reaction of perfluorinated arenes with aryl boronate esters using NHC nickel complexes as catalysts is described. The efficiencies of different boronate esters (p-tolyl-Beg, p-tolyl-Bneop, p-tolyl-Bpin, p-tolyl-Bcat) and the corresponding boronic acid (p-tolyl-B(OH)2) in this type of cross-coupling reaction were evaluated (eg, ethyleneglycolato; neop, neopentylglycolato;

  描述了使用NHC镍络合物作为催化剂的全氟化芳烃与芳基硼酸酯的有效Suzuki-Miyaura交叉偶联反应。不同的硼酸酯的效率（p甲苯基-初学者，p甲苯基- Bneop，p甲苯基- BPIN，p甲苯基- BCAT）和相应的硼酸（p甲苯基- B（OH）2在这种类型的）评估了交叉偶联反应的百分数（例如，乙二醇乙二醇； neop，新戊基乙二醇乙酸； pin，pinacolato； cat，catecholato）。研究表明，芳基-Beg是最活泼的硼酸酯。使用CsF作为添加剂对于六氟苯与芳基新戊基乙二醇硼酸酯的有效反应至关重要。
• Photoredox/Nickel Dual-Catalyzed Reductive Cross Coupling of Aryl Halides Using an Organic Reducing Agent
  作者：Abhishek Dewanji、Raoul F. Bülow、Magnus Rueping

  DOI：10.1021/acs.orglett.0c00199

  日期：2020.2.21

  cross-coupling of polyfluorinated arenes with a broad range of aryl halides has been developed. Sequential carbon-fluorine bond cleavage and carbon-carbon bond formation are two of the important features of the reaction. Addition of an aryl radical anion to a nickel intermediate was achieved for the first time using polyfluoroarenes as radical precursors. This, in combination with the excellent para selectivity

  已经开发出一种成功的方案，用于将多氟芳烃与广泛的芳基卤化物进行还原性芳基-芳基交叉偶联。顺序的碳-氟键断裂和碳-碳键形成是反应的两个重要特征。使用多氟芳烃作为自由基前体，首次实现了将芳基自由基阴离子加到镍中间体上。结合出色的对位选择性，为各种新的多氟化联芳基化合物的合成铺平了道路。