2-(4'-methyl-[1,1'-biphenyl]-2-yl)pyridine

• 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'-methyl-[1,1'-biphenyl]-2-yl)pyridine
• 英文别名: 2-[2-(4-methylphenyl)]phenylpyridine；2-(4’-methyl-[1,1’-biphenyl]-2-yl)pyridine；2-(4′-methyl-[1,1′-biphenyl]-2-yl)pyridine；2-[2-(4-Methylphenyl)phenyl]pyridine
• 化学式: C₁₈H₁₅N
• 分子量: 245.324
• InChiKey: DKIBUFBAMGZCBK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-(4'-methyl-[1,1'-biphenyl]-2-yl)pyridine 在 氢化钾 作用下， 以 甲苯 为溶剂， 以60 %的产率得到6-Methylphenanthro[9,10-b]pyridine
  参考文献：
  名称：

  2-苯基吡啶逐步C-H芳基化还原环化脱氢合成二苯并[f,h]喹啉

  摘要：

  介绍了一种通过逐步钌催化的 C-H 芳基化和钾介导的还原性环化脱氢从 2-苯基吡啶和芳基溴化物合成二苯并 [f, h] 喹啉及其衍生物的方法。一种二苯并[ f , h ] 喹啉衍生物被用作双齿配体来制备环金属化的钌络合物。通过单晶 X 射线结构分析表征了两种二苯并 [ f , h ] 喹啉化合物和钌络合物。

  DOI：

  10.1055/a-2069-4269
• 作为产物：
  描述：

  三正丁基2-吡啶基锌 在 bis(1,5-cyclooctadiene)nickel (0) 、 四(三苯基膦)钯 、 cesium fluoride 、 三环己基膦 作用下， 以 甲苯 为溶剂， 反应 12.0h， 生成 2-(4'-methyl-[1,1'-biphenyl]-2-yl)pyridine
  参考文献：
  名称：

  Nickel-Catalyzed Suzuki–Miyaura Reaction of Aryl Fluorides

  摘要：

  Two protocols for the nickel-catalyzed cross-coupling of aryl fluorides with aryl boronic esters have been developed. The first employs metal fluoride cocatalysts, such as ZrF4 and TiF4, which enable Suzuki-Miyaura reactions of aryl fluorides bearing electron-withdrawing (ketones, esters, and CF3), aryl and alkenyl groups as well as those comprising fused aromatic rings, such as fluoronaphthalenes and fluoroquinolines. The second protocol employs aryl fluorides bearing ortho-directing groups, which facilitate the difficult C-F bond activation process via cyclometalation. N-heterocycles, such as pyridines, quinolines, pyrazoles, and oxazolines, can successfully promote cross-coupling with an array of organoboronic esters. A study into the substituent effects with respect to both coupling components has provided fundamental insights into the mechanism of the nickel-catalyzed cross-coupling of aryl fluorides.

  DOI：

  10.1021/ja207759e

文献信息

• Solvent and Base in One: Tetra-<i>n</i> -butylammonium Acetate as a Multi-Purpose Ionic Liquid Medium for Ru-Catalyzed Directed Mono- and Di-<i>o</i> -C-H Arylation Reactions
  作者：Ya-Ling Zou、Zhen-Yu Wang、Yin-Mao Feng、You-Gui Li、Eric Assen B. Kantchev

  DOI：10.1002/ejoc.201701022

  日期：2017.11.16

  Bu4NOAc can be a multi-purpose medium for a Ru-catalyzed directed o-C–H arylation reaction with functionalized aryl bromides. Acetate plays the role of base and Bu4N salts (excess acetate and side product bromide) behave as ionic liquids. The medium is compatible with both RuCl3·xH2O (major product: di-arylation) and [RuCl2(p-cymene)]2/(p-Tol)3P catalytic systems (major product: mono-arylation).

  Bu 4 NOAc可以是多官能团介质，用于Ru催化的与官能化芳基溴化物进行的定向o -C–H芳基化反应。乙酸盐起碱的作用，Bu 4 N盐（过量的乙酸盐和副产物溴化物）起离子液体的作用。该介质与RuCl 3 · x H 2 O（主要产物：二芳基化）和[RuCl 2（p- cymene）] 2 /（p -Tol）3 P催化系统兼容（主要产物：单芳基化） 。
• Hydrophilic (η⁶-Arene)–Ruthenium(II) Complexes with P–OH Ligands as Catalysts for the Isomerization of Allylbenzenes and C–H Bond Arylation Reactions in Water
  作者：Rebeca González-Fernández、Pascale Crochet、Victorio Cadierno

  DOI：10.1021/acs.organomet.9b00463

  日期：2019.10.14

  Half-sandwich ruthenium(II) complexes containing η6-coordinated 3-phenylpropanol and phosphinous-acid-type ligands, namely, [RuCl2(η6-C6H5CH2CH2CH2OH)P(OH)R2}] (R = Me (2a), Ph (2b), 4-C6H4CF3 (2c), 4-C6H4OMe (2d), OMe (2e), OEt (2f), and OPh (2g), have been synthesized in 44–88% yield by reacting [RuCl2η6:κ1(O)-C6H5CH2CH2CH2OH}] (1) with the appropriate pentavalent phosphorus oxide R2P(═O)H. The

  含η半夹心钌（II）配合物6配位的3-苯基丙醇和亚膦酸基型配体，即，将[RuCl 2（η 6 -C 6 H ^ 5 CH 2 CH 2 CH 2 OH）P（OH） R 2 }]（R = Me（2a），Ph（2b），4-C 6 H 4 CF 3（2c），4-C 6 H 4 OMe（2d），OMe（2e），OEt（2f），和OPh（2克），已在44-88％的产率通过反应而合成将[RuCl 2 η 6：κ 1（Ò）-C 6 H ^ 5 CH 2 CH 2 CH 2 OH}]（1）与适当的五价磷氧化物R 2 P（＝ O）H。的结构将[RuCl 2（η 6 -C 6 H ^ 5 CH 2 CH 2 CH 2 OH）P（OH）Me 2 }]（2A）通过X射线衍射方法进行了明确地证实。化合物2a – g被证明是催化活性在allylbenzenes的异构化为相应的（1-丙烯基）采用水作为唯一的反应溶剂，用将[RuCl苯衍生物2（η
• Palladium-Catalyzed Direct <i>Ortho</i> C–H Arylation of 2-Arylpyridine Derivatives with Aryltrimethoxysilane
  作者：Wu Li、Zhangwei Yin、Xiaoqing Jiang、Peipei Sun

  DOI：10.1021/jo2016168

  日期：2011.10.21

  A Pd(OAc)2-catalyzed cross-coupling reaction between 2-arylpyridine and aryltrimethoxysilane in the presence of AgF and BQ in 1,4-dioxane was studied. After various reaction parameters (catalyst, oxidant, additive, solvent and reaction temperature) were examined, the optimal conditions for the reaction were identified. The synthesis is compatible to aryltrimethoxysilane with both electron-withdrawing

  研究了在1，4-二恶烷中，在AgF和BQ存在下，Pd（OAc）2催化2-芳基吡啶与芳基三甲氧基硅烷之间的交叉偶联反应。在检查了各种反应参数（催化剂，氧化剂，添加剂，溶剂和反应温度）后，确定了反应的最佳条件。该合成与芳基三甲氧基硅烷在芳基部分上具有吸电子基团和给电子基团两者相容，且产率适中。提供了C–H键活化的动力学同位素效应（k H / k D）。
• Directed Palladium-Catalyzed Oxidative C-H Arylation of (Hetero)arenes with Arylboronic Acids by Using TEMPO
  作者：Armido Studer、Sylvia Kirchberg、Thomas Vogler

  DOI：10.1055/s-0028-1083546

  日期：——

  Oxidative coupling of three different arenes and a thiophene derivative with various arylboronic acids with Pd(OAc) 2 and the commercially available 2,2,6,6-tetramethylpiperidine-N-oxyl radical (TEMPO) as an oxidant are reported. A 2-pyridyl group on the substrates serves as ortho-directing group to mediate the C-H arylation. Mechanistic studies are provided.

  报道了三种不同的芳烃和噻吩衍生物与各种芳基硼酸与 Pd(OAc) 2 和作为氧化剂的市售 2,2,6,6-四甲基哌啶-N-氧基自由基 (TEMPO) 的氧化偶联。底物上的 2-吡啶基用作邻位导向基团以介导 CH 芳基化。提供了机理研究。
• C−H Bond Activation/Arylation Catalyzed by Arene-Ruthenium-Aniline Complexes in Water
  作者：Chinky Binnani、Deepika Tyagi、Rohit K. Rai、Shaikh M. Mobin、Sanjay K. Singh

  DOI：10.1002/asia.201600954

  日期：2016.11.7

  Water‐soluble arene–ruthenium complexes coordinated with readily available aniline‐based ligands were successfully employed as highly active catalysts in the C−H bond activation and arylation of 2‐phenylpyridine with aryl halides in water. A variety of (hetero)aryl halides were also used for the ortho‐C−H bond arylation of 2‐phenylpyridine to afford the corresponding ortho‐ monoarylated products as

  水溶性芳烃-钌配合物与现成的苯胺基配体配合使用已成功地用作高活性催化剂，用于CH键活化和2-苯基吡啶与芳基卤化物的芳基化反应。各种（杂）芳基卤化物也用于2-苯基吡啶的邻位C-H键芳基化反应，以提供相应的邻位单芳基化产品作为主要产品，产量中等至良好。我们的研究（包括时标NMR光谱和质谱研究）表明，具有苯胺基配位基的配体具有不同的电子和空间特性，对所得芳烃-钌-苯胺基配合物的催化活性具有重要影响。此外，cycloruthenated物种的质谱鉴定，（η 6 -arene）的Ru（κ 2 - ç，Ñ -phenylpyridine）} +，和几个配位体配位的cycloruthenated物种，如[（η 6 -arene）的Ru（ -4-甲基苯胺）（κ 2 - ç，ñ -phenylpyridine）]在2-苯基吡啶与芳烃-钌-苯胺络合物反应过程中发现的+，进一步证实了这些物种在观察到的高活性和