2,4,6-trifluoro-4'-methoxybiphenyl | 1206164-33-1

• 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: 2,4,6-trifluoro-4'-methoxybiphenyl
• 英文别名: 2,4,6-trifluoro-4'-methoxy-1,1'-biphenyl；1,3,5-Trifluoro-2-(4-methoxyphenyl)benzene
• CAS: 1206164-33-1
• 化学式: C₁₃H₉F₃O
• 分子量: 238.209
• InChiKey: XRTMAEMGYCQJAI-UHFFFAOYSA-N

物化性质

• 沸点：
  268.8±40.0 °C(Predicted)
• 密度：
  1.244±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2,4,6-三氟苯甲酸 在 (1,5-环辛二烯)二(三甲基硅烷基甲基)钯(II) 、 sodium t-butanolate 、 2-二环己基磷-2,4,6-三异丙基联苯 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 反应 26.0h， 生成 2,4,6-trifluoro-4'-methoxybiphenyl
  参考文献：
  名称：

  无添加剂钯催化的芳基氯化物的脱羧交叉偶联

  摘要：

  （杂）芳基羧酸钠与（杂）芳基氯化物的交叉偶联用1mol％的钯催化剂进行，不需要无机碱，银盐或铜盐。这种耦合使用两个低能伙伴，唯一的化学计量副产物是二氧化碳和氯化钠。底物范围包括较少活化的芳基氯化物和羧酸盐（> 25个实例）。钯的负载量可以降低到0.1mol％，并且可以使用布赫瓦尔德（Buchwald）型预催化剂。

  DOI：

  10.1021/acs.orglett.9b01620

文献信息

• Copper-Catalyzed Decarboxylative Cross-Coupling of Potassium Polyfluorobenzoates with Aryl Iodides and Bromides
  作者：Rui Shang、Yao Fu、Yan Wang、Qing Xu、Hai-Zhu Yu、Lei Liu

  DOI：10.1002/anie.200904916

  日期：2009.11.23

  For copper only: The decarboxylative cross‐coupling of readily accessible and nonvolatile potassium polyfluorobenzoates with aryl iodides and bromides using a copper catalyst provides polyfluorobiaryls and polyfluorostilbenes in excellent yields (see scheme). Mechanistic analyses are reported for the title reaction.

  仅适用于铜：使用铜催化剂，易于获得且不挥发的多氟苯甲酸钾与芳基碘化物和溴化物的脱羧交叉偶联可提供极佳的收率的多氟联芳基和多氟苯磺酸酯（请参见方案）。报告了标题反应的机理分析。
• Pd-Catalyzed Decarboxylative Cross Coupling of Potassium Polyfluorobenzoates with Aryl Bromides, Chlorides, and Triflates
  作者：Rui Shang、Qing Xu、Yuan-Ye Jiang、Yan Wang、Lei Liu

  DOI：10.1021/ol100008q

  日期：2010.3.5

  Pd-catalyzed decarboxylative cross coupling of potassium polyfluorobenzoates with aryl bromides, chlorides, and triflates is achieved by using diglyme as the solvent. The reaction is useful for synthesis of polyfluorobiaryls from readily accessible and nonvolatile polyfluorobenzoate salts. Unlike the Cu-catalyzed decarboxylation cross coupling where oxidative addition is the rate-limiting step, in

  通过使用二甘醇二甲醚作为溶剂可实现多氟苯甲酸钾与芳基溴化物，氯化物和三氟甲磺酸酯的钯催化脱羧交叉偶联。该反应可用于由容易获得的非挥发性多氟苯甲酸盐合成多氟联芳基。与其中氧化加成是限速步骤的Cu催化的脱羧交叉偶联不同，在Pd催化的形式中，脱羧是限速步骤。
• Combined Experimental and Computational Mechanistic Investigation of the Palladium-Catalyzed Decarboxylative Cross-Coupling of Sodium Benzoates with Chloroarenes
  作者：Jenna N. Humke、Ryan A. Daley、Aaron S. Morrenzin、Sharon R. Neufeldt、Joseph J. Topczewski

  DOI：10.1021/acs.joc.1c00910

  日期：2021.9.3

  is a mechanistic investigation into the palladium-catalyzed decarboxylative cross-coupling of sodium benzoates and chloroarenes. The reaction was found to be first-order in Pd. A minimal substituent effect was observed with respect to chloroarene, and the reaction was zero-order with respect to chloroarene. Palladium-mediated decarboxylation was assigned as the turnover-limiting step based on an Eyring

  本文报道了对钯催化的苯甲酸钠和氯芳烃的脱羧交叉偶联的机理研究。发现反应在 Pd 中是一级反应。观察到对氯芳烃的取代作用最小，对氯芳烃反应为零级。基于艾林图和密度泛函理论计算，钯介导的脱羧被指定为转换限制步骤。发现催化剂性能因亲电试剂而异，这最好通过催化剂在 Pd(0) 处分解来解释。的1,5-环辛二烯（COD）的配体包含在前段催化剂CODPd（CH 2 TMS）2（PD1）被证明是有益的添加剂。长凳稳定的 Buchwald 复合体XPhosPdG2可以与外源COD和2-二环己基膦基-2'，4'，6'-三异丙基联苯（XPhos）代替复杂的使用PD1。添加外源 XPhos 显着增加了催化剂周转数并增强了重现性。
• A New Palladium Precatalyst Allows for the Fast Suzuki−Miyaura Coupling Reactions of Unstable Polyfluorophenyl and 2-Heteroaryl Boronic Acids
  作者：Tom Kinzel、Yong Zhang、Stephen L. Buchwald

  DOI：10.1021/ja1073799

  日期：2010.10.13

  Boronic acids which quickly deboronate under basic conditions, such as polyfluorophenylboronic acid and five-membered 2-heteroaromatic boronic acids, are especially challenging coupling partners for Suzuki-Miyaura reactions. Nevertheless, being able to use these substrates is highly desirable for a number of applications. Having found that monodentate biarylphosphine ligands can promote these coupling processes, we developed a precatalyst that forms the catalytically active species under conditions where boronic acid decomposition is slow. With this precatalyst, Suzuki-Miyaura reactions of a wide range of (hetero)aryl chlorides, bromides, and triflates with polyfluorophenyl, 2-furan, 2-thiophene, and 2-pyrroleboronic acids and their analogues proceed at room temperature or 40 degrees C in short reaction times to give the desired products in excellent yields.
• Palladium nanocrystals stabilized by cucurbit[6]uril as efficient heterogeneous catalyst for direct C–H functionalization of polyfluoroarenes
  作者：Minna Cao、Dongshuang Wu、Weiping Su、Rong Cao

  DOI：10.1016/j.jcat.2014.10.013

  日期：2015.1

  Palladium nanocrystals (Pd NCs) featuring abundant surface defects are successfully synthesized by using cucurbit[6]uril as a stabilizer. Employing the as-prepared Pd NCs as catalyst, an efficient approach to the direct C-H functionalization of electron-deficient polyfluoroarenes has been developed. The stable Pd NCs catalyst exhibits excellent catalytic activity and good recyclability with significantly low catalyst loading. The catalytic procedure is insensitive to air and moisture and can be manipulated under ambient environment with operational ease. Mechanistic experiments have provided credible data to support a heterogeneous catalytic mechanism of the present system. (C) 2014 Elsevier Inc. All rights reserved.