N,N-dimethyl-2'-(pyridin-2-yl)-[1,1'-biphenyl]-4-amine | 1234421-77-2

• 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: N,N-dimethyl-2'-(pyridin-2-yl)-[1,1'-biphenyl]-4-amine
• 英文别名: N,N-dimethyl-4-(2-pyridin-2-ylphenyl)aniline
• CAS: 1234421-77-2
• 化学式: C₁₉H₁₈N₂
• 分子量: 274.365
• InChiKey: IJVGIXJRSMNYMW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  16.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 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 2.0h， 生成 N,N-dimethyl-2'-(pyridin-2-yl)-[1,1'-biphenyl]-4-amine
  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

• 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
• Ligand‐Tuned C–H Bond Activation/Arylation of 2‐Arylpyridines over Pyridine‐Based <i>N</i> , <i>O/N</i> , <i>N</i> Ligated Ruthenium–Arene Complexes
  作者：Chinky Binnani、Rohit K. Rai、Deepika Tyagi、Shaikh M. Mobin、Sanjay K. Singh

  DOI：10.1002/ejic.201701446

  日期：2018.3.29

  our investigations, including time‐dependent 1H NMR spectroscopic studies with ruthenium–arene catalysts, demonstrate a remarkable structure–activity relationship for the ligand‐tuned C–H activation/arylation of 2‐phenylpyridine, where the complexes with bischelating N,O donor‐based ligands (acteylpyridine and picolinate) outperform those with N,N donor ligands (iminopyridine). Moreover, among the N

  水溶性钌（II）配合物-arene [（η 6 -arene）的Ru（κ 2 -L）] ñ +（Ñ = 0，1）（的[Ru] -1 - [茹] -10）含吡啶合成了基于双螯合的N，O / N，N供体配体（L1 - L5），并用于水中各种2-苯基吡啶和卤代芳基的C-H键催化活化/芳基化，提供了相应的单-和-二芳基化产品。探索合成配合物的反应性，我们的研究包括时间依赖性1用钌-芳烃催化剂进行的1 H NMR光谱研究表明，对2-苯基吡啶的配体调谐C–H活化/芳基化具有显着的结构-活性关系，其中配合物具有双螯合的N，O供体基配体（乙酰吡啶和吡啶甲酸）优于具有N，N个供体配体（亚氨基吡啶）的那些。此外，在N，O供体配体中，还观察到配位氧供体的性质对催化活性的显着影响，其中具有N，O的钌-芳烃配合物具有中性氧供体原子的供体配体（乙酰基吡啶）比具有阴离子氧供体原子（吡啶甲酸）的配体具有更高的催化活性。观
• Ruthenium(<scp>ii</scp>)-catalyzed selective monoarylation in water and sequential functionalisations of C–H bonds
  作者：Percia B. Arockiam、Cédric Fischmeister、Christian Bruneau、Pierre H. Dixneuf

  DOI：10.1039/c2gc36222h

  日期：——

  The ruthenium(II)-phosphine catalyst RuCl2(PPh3)(p-cymene) operating water selectively leads to ortho monoarylation, with arylchlorides and heteroarylhalides, of functional arenes. Further catalytic heteroarylation with Ru(OAc)2(p-cymene) in water produces mixed bifunctional derivatives.

  铑(II)-膦催化剂RuCl2(PPh3)(p-cymene)在水中选择性地进行邻位单芳基化，适用于功能性芳烃与芳基氯化物和杂芳基卤化物的反应。此外，使用Ru(OAc)2(p-cymene)在水中进一步催化杂芳基化会产生混合的双功能衍生物。
• Pyridine-directed carbon–carbon single bond activation: Rhodium-catalyzed decarbonylation of aryl and heteroaromatic ketones
  作者：Cole J. Wagner、Eric A. Salisbury、Erik J. Schoonover、Jacob P. VanderRoest、Jeffrey B. Johnson

  DOI：10.1016/j.tetlet.2021.153132

  日期：2021.6

  The decarbonylation of 2-pyridyl-substituted ketones via transition metal-catalyzed carbon–carbon bond activation provides ready access to a variety of biaryl compounds. The highly efficient and general method provides reliable decarbonylation of benzophenones including a range of functional groups and substitution patterns. The methodology has also proven highly efficient for heteroaromatic substrates

  通过过渡金属催化的碳-碳键活化使 2-吡啶基取代的酮脱羰，可以很容易地获得各种联芳基化合物。高效且通用的方法提供了可靠的二苯甲酮脱羰，包括一系列官能团和取代模式。该方法还被证明对杂芳族底物非常有效，包括那些含有苯硫基、吲哚基、喹啉基和吡啶取代的底物。
• A Highly Efficient Ruthenium(II) Catalyst with (1,2-Diarylvinyl)phosphine Ligands for Direct Ortho Arylation of 2-Arylpyridine with Aryl Chlorides
  作者：Bingran Yu、Xiaoyu Yan、Song Wang、Ning Tang、Chanjuan Xi

  DOI：10.1021/om100407q

  日期：2010.7.26

  were synthesized, and their ruthenium complexes have been prepared. The structure of [(1,2-diphenylvinyl)phosphine](η6-cymene)RuCl2 (C1) was confirmed by X-ray crystallography. Ruthenium (1,2-diarylvinyl)phosphine complexes are highly efficient catalysts for direct ortho arylation of 2-arylpyridine with a range of aryl chlorides (electron-rich and electron-poor aromatic chlorides). Highly controllable

  合成了一系列的（1,2-二芳基乙烯基）膦配体，并制备了它们的钌配合物。的结构[（1,2-二苯基乙烯基）膦]（η 6 -cymene）的RuCl 2（C1）通过X-射线结晶学证实。钌（1,2-二芳基乙烯基）膦配合物是用于2-芳基吡啶与一系列芳基氯化物（富电子和贫电子芳族氯化物）直接邻位芳基化的高效催化剂。通过芳香环上CH键的官能化，高度可控地形成单芳基化和二芳基化。