2-(3,4'-dimethyl-[1,1'-biphenyl]-2-yl)pyridine | 1234421-86-3

• 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-(3,4'-dimethyl-[1,1'-biphenyl]-2-yl)pyridine
• 英文别名: 2-[2-Methyl-6-(4-methylphenyl)phenyl]pyridine；2-[2-methyl-6-(4-methylphenyl)phenyl]pyridine
• CAS: 1234421-86-3
• 化学式: C₁₉H₁₇N
• 分子量: 259.351
• InChiKey: KUDHFLUICWVQNE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2-(邻甲苯)吡啶 在 硫酸 、 碘 、 palladium diacetate 、 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 6.5h， 生成 2-(3,4'-dimethyl-[1,1'-biphenyl]-2-yl)pyridine
  参考文献：
  名称：

  Catalytic Electrochemical C–H Iodination and One-Pot Arylation by ON/OFF Switching of Electric Current

  摘要：

  Palladium-catalyzed electrochemical iodination and one-pot arylation of arylpyridines are described. Ortho-selective C-H iodination proceeded via dual activation of each substrate by a palladium catalyst and an electrode. Various aryl groups were introduced at the ortho positions of arylpyridines by ON/OFF switching of two different catalytic cycles using the same palladium catalyst in a one-pot fashion.

  DOI：

  10.1021/jo3012286

文献信息

• Iridium(III)-Catalyzed Direct Arylation of C–H Bonds with Diaryliodonium Salts
  作者：Pan Gao、Wei Guo、Jingjing Xue、Yue Zhao、Yu Yuan、Yuanzhi Xia、Zhuangzhi Shi

  DOI：10.1021/jacs.5b06758

  日期：2015.9.30

  arylation of complex compounds. Mechanistic studies by density functional theory calculations suggested that the sp(3) C-H activation was realized by a triflate-involved concerted metalation-deprotonation process, and the following oxidation of Ir(III) to Ir(V) is the most favorable when a bistriflimide is contained in the diaryliodonium salt. Calculations indicated that both steps are enabled by initial anion

  通过开发一种新的 Ir(III) 催化的 CC 交叉偶联，已经建立了一种将酮肟、含氮杂环、各种芳烃和烯烃中的 sp(2) 和 sp(3) CH 键直接芳基化的通用方法。该芳基化的关键取决于适当的催化剂选择和使用二芳基碘鎓Triflate Salts作为偶联伴侣。这种转化具有良好的官能团兼容性，可以作为复杂化合物后期 CH 芳基化的有力合成工具。通过密度泛函理论计算的机理研究表明 sp(3) CH 活化是通过三氟甲磺酸酯参与的协同金属化-去质子化过程实现的，当双氟甲磺酰亚胺包含在二芳基碘鎓盐中。
• Photo‐Induced Ruthenium‐Catalyzed C−H Arylations at Ambient Temperature
  作者：Korkit Korvorapun、Julia Struwe、Rositha Kuniyil、Agnese Zangarelli、Anna Casnati、Marjo Waeterschoot、Lutz Ackermann

  DOI：10.1002/anie.202003035

  日期：2020.10.5

  Ambient temperature ruthenium‐catalyzed C−H arylations were accomplished by visible light without additional photocatalysts. The robustness of the ruthenium‐catalyzed C−H functionalization protocol was reflected by a broad range of sensitive functional groups and synthetically useful pyrazoles, triazoles and sensitive nucleosides and nucleotides, as well as multifold C−H functionalizations. Biscyclometalated

  环境温度钌催化的 C−H 芳基化反应是通过可见光完成的，无需额外的光催化剂。钌催化的 C−H 官能化方案的稳健性体现在广泛的敏感官能团和合成上有用的吡唑、三唑和敏感核苷和核苷酸，以及多重 C−H 官能化。通过详细的计算和实验机理分析，双环金属化钌配合物被确定为光氧化还原钌催化中的关键中间体。计算表明，原位形成的光活性钌物质优选经历内球电子转移。
• Ru-catalyzed aerobic oxidative coupling of arylboronic acids with arenes
  作者：Hong Li、Wei Wei、Yuan Xu、Chao Zhang、Xiaobing Wan

  DOI：10.1039/c0cc04322b

  日期：——

  A Ru-catalyzed oxidative coupling of arenes with boronic acids using molecular oxygen via direct C-H activation is reported. Both the scope and the mechanism of the process are discussed.

  据报道，使用分子氧通过直接CH活化，Ru催化了芳烃与硼酸的氧化偶联。讨论了过程的范围和机制。
• One‐Pot Tandem Photoredox and Cross‐Coupling Catalysis with a Single Palladium Carbodicarbene Complex
  作者：Yu‐Cheng Hsu、Vincent C.‐C. Wang、Ka‐Chun Au‐Yeung、Chung‐Yu Tsai、Chun‐Chi Chang、Bo‐Chao Lin、Yi‐Tsu Chan、Chao‐Ping Hsu、Glenn P. A. Yap、Titel Jurca、Tiow‐Gan Ong

  DOI：10.1002/anie.201800951

  日期：2018.4.16

  transition‐metal‐catalyzed coupling (2 e− process) and photoredox catalysis (1 e− process) has emerged as a powerful approach to catalyze difficult cross‐coupling reactions under mild reaction conditions. Reported is a palladium carbodicarbene (CDC) complex that mediates both a Suzuki–Miyaura coupling and photoredox catalysis for C−N bond formation upon visible‐light irradiation. These two catalytic pathways

  常规的过渡金属催化的偶联（2的组合 ë -和photoredox催化（1过程）  ë -处理）已经成为一种强有力的方法来催化温和反应条件下难以交叉偶联反应。报道了一种钯碳二碳烯（CDC）复合物，它在可见光照射下介导铃木-宫浦偶合和光氧化还原催化C-N键的形成。这两种催化途径可以结合起来，以促进传统的过渡金属催化的偶合和光氧化还原催化，在环境条件下用单一催化剂在高效的一锅法中介导CH芳基化。
• Stoichiometric to catalytic reactivity of the aryl cycloaurated species with arylboronic acids: insight into the mechanism of gold-catalyzed oxidative C(sp²)–H arylation
  作者：Qian Wu、Chenglong Du、Yumin Huang、Xingyan Liu、Zhen Long、Feijie Song、Jingsong You

  DOI：10.1039/c4sc02070g

  日期：——

  and 3b) and [AuBr(Ph)(tpy)] (7), as well as the aryl gold(III) complex [AuCl2(Ph)(tpy)] (8) (tpy = 2-(o-tolyl)pyridine) as reliable models, we present a detailed study of the mechanism for gold(III)-catalyzed oxidative cross-coupling reactions between cycloaurable arenes and arylboronic acids. Here we report the direct evidence for a mechanistic proposal including arene C–H activation, transmetallation

  基于明确的五元芳基金 ( III ) 配合物，[Au(tpy)X 2 ] ( 3a和3b ) 和 [AuBr(Ph)(tpy)] ( 7 )，以及芳基金 ( III ) 配合物 [AuCl 2 (Ph)(tpy)] ( 8 ) (tpy = 2-( o -tolyl)pyridine) 作为可靠的模型，我们对金 ( III ) 催化的氧化交叉反应机理进行了详细研究。可环芳芳烃和芳基硼酸之间的偶联反应。在这里，我们报告了机制建议的直接证据，包括芳烃 C-H 活化、金属转移和联芳基还原消除。螯合辅助的 C-H 活化策略已用于开发金 ( III ) 催化的芳烃与芳基试剂的 C-H 键芳基化，以形成扩展的 π 共轭体系。