2-(3'-methylbiphenyl-2-ylsulfinyl)pyridine | 1329491-64-6

• 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'-methylbiphenyl-2-ylsulfinyl)pyridine
• 英文别名: 2-[2-(3-Methylphenyl)phenyl]sulfinylpyridine
• CAS: 1329491-64-6
• 化学式: C₁₈H₁₅NOS
• 分子量: 293.389
• InChiKey: MVSCCIJOQURRKY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  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：
  0.06
• 拓扑面积：
  49.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(3'-methylbiphenyl-2-ylsulfinyl)pyridine 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.75h， 以91%的产率得到3-甲基联苯
  参考文献：
  名称：

  Palladium-Catalyzed Coupling of Arene C–H Bonds with Methyl- and Arylboron Reagents Assisted by the Removable 2-Pyridylsulfinyl Group

  摘要：

  The Pd-II-catalyzed direct coupling of arene C-H bonds with organoboron reagents assisted by the 2-pyridylsulfinyl group is reported. Methylboronic acid and arylboronic acid neopentyl esters proved to be efficient coupling partners, furnishing methylated arenes and biaryl products in moderate to good yields. The 2-pyridylsulfinyl group can be easily removed to provide the free biaryls. The essential role of the 2-pyridyl unit in stabilizing the cyclopalladation complex was demonstrated by X-ray diffraction analysis of the palladacycle intermediate.

  DOI：

  10.1021/jo2018137
• 作为产物：
  描述：

  2-苯硫基吡啶 在 palladium diacetate 、 溶剂黄146 、 silver carbonate 、 对苯醌 作用下， 以 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 13.5h， 生成 2-(3'-methylbiphenyl-2-ylsulfinyl)pyridine
  参考文献：
  名称：

  可移动的2-吡啶基亚磺酰基辅助的钯催化的芳烃CH键区域选择性芳基化

  摘要：

  描述了由可除去的2-吡啶基亚磺酰基协助的芳烃CH键的钯催化的芳基化。该反应使用芳基三氟硼酸酯作为芳基化试剂，从而以中等至良好的产率得到了具有宽底物范围的相应产物。可以除去指导基团或将其转换为其他有用的功能，这证明了该方法的潜在综合应用。 CH键活化-芳基化-芳基三氟硼酸酯-亚砜-钯催化

  DOI：

  10.1055/s-0031-1290320

文献信息

• Palladium(II)-Catalyzed Direct Alkenylation and Arylation of Arenes: Removable 2-Pyridylsulfinyl Group Assisted C–H Bond Activation
  作者：Ming Yu、Zunjun Liang、Yongyong Wang、Yuhong Zhang

  DOI：10.1021/jo200666z

  日期：2011.6.17

  Palladium-catalyzed C–H activation reactions directed by a removable 2-pyridylsulfinyl group were developed. Aromatic olefination products were formed in good yields on treatment of 2-(phenylsulfinyl)pyridines with alkenes in the presence of a Pd catalyst. The reaction tolerates a wide range of substituted alkenes, including various acrylates and styrenes. The controlled experiments indicated that

  钯催化的可移动的2-吡啶基亚磺酰基基团引起的CH活化反应得以开发。在Pd催化剂存在下，用烯烃处理2-（苯基亚磺酰基）吡啶，以高收率形成芳族烯烃化产物。该反应可耐受各种取代的烯烃，包括各种丙烯酸酯和苯乙烯。对照实验表明2-吡啶基部分而不是亚磺酰基起配体的作用。最终的还原性脱磺酰化分别提供了具有不同还原条件的对苯二甲酸酯，硫化物和二硫化物。更重要的是，这种转换也可以通过双重C–H激活而应用于芳基化反应中。
• Palladium-catalyzed decarboxylative ortho-arylation of 2-pyridyl sulfoxides with benzoyl peroxides
  作者：Meng Sun、Zhe Wang、Jiaxin Wang、Peiyu Guo、Xiangxiang Chen、Ya-Min Li

  DOI：10.1039/c6ob02040b

  日期：——

  A palladium catalyzed efficient strategy for regio-selective ortho-arylation of sulfoxides with benzoyl peroxides via decarboxylation has been developed. This reaction proceeds smoothly, tolerates a variety of functional groups, and provides easy access to the synthesis of different biaryl compounds.

  钯催化效率的战略区域选择性的邻苯甲酰过氧化物亚砜的-arylation通过脱羧已经研制成功。该反应顺利进行，可耐受各种官能团，并易于合成不同的联芳基化合物。
• Palladium-Catalyzed Regioselective Arylation of Arene C-H Bond Assisted by the Removable 2-Pyridylsulfinyl Group
  作者：Yuhong Zhang、Xunbin Zhang、Ming Yu、Jinzhong Yao

  DOI：10.1055/s-0031-1290320

  日期：2012.2

  A palladium-catalyzed arylation of arene C-H bond assisted by a removable 2-pyridylsulfinyl group is described. The reaction employs aryltrifluoroborates as the arylation reagent, leading to the corresponding products in moderate to good yield with broad substrate scope. The directing group can be removed or converted to other useful functionalities, which showcases the potential synthetic application

  描述了由可除去的2-吡啶基亚磺酰基协助的芳烃CH键的钯催化的芳基化。该反应使用芳基三氟硼酸酯作为芳基化试剂，从而以中等至良好的产率得到了具有宽底物范围的相应产物。可以除去指导基团或将其转换为其他有用的功能，这证明了该方法的潜在综合应用。 CH键活化-芳基化-芳基三氟硼酸酯-亚砜-钯催化
• Palladium-Catalyzed Coupling of Arene C–H Bonds with Methyl- and Arylboron Reagents Assisted by the Removable 2-Pyridylsulfinyl Group
  作者：José A. Romero-Revilla、Alfonso Garcı́a-Rubia、Ramón Goméz Arrayás、M. Ángeles Fernández-Ibáñez、Juan C. Carretero

  DOI：10.1021/jo2018137

  日期：2011.11.18

  The Pd-II-catalyzed direct coupling of arene C-H bonds with organoboron reagents assisted by the 2-pyridylsulfinyl group is reported. Methylboronic acid and arylboronic acid neopentyl esters proved to be efficient coupling partners, furnishing methylated arenes and biaryl products in moderate to good yields. The 2-pyridylsulfinyl group can be easily removed to provide the free biaryls. The essential role of the 2-pyridyl unit in stabilizing the cyclopalladation complex was demonstrated by X-ray diffraction analysis of the palladacycle intermediate.