2-(2-(p-tolylthio)phenyl)pyridine | 1584673-16-4

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 2-(2-(p-tolylthio)phenyl)pyridine
• CAS: 1584673-16-4
• 化学式: C₁₈H₁₅NS
• 分子量: 277.39
• InChiKey: REJOYZFNVYYJKX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.21
• 重原子数：
  20.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  12.89
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  对甲苯二硫醚 在 双(乙腈)氯化钯(II) 、 sodium hydride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 60.0h， 生成 2-(2-(p-tolylthio)phenyl)pyridine
  参考文献：
  名称：

  Pd(II)-catalyzed selective sulfenylation of arene C–H bonds using N-arylthiobenzamides as thiolation reagent and oxidant

  摘要：

  The palladium-catalyzed direct sulfenylation of arenes with N-arylthiobenzamides was developed for the synthesis of aryl sulfides. Additional oxidant was not required for the catalytic cycle because N-arylthiobenzamide was used as both thiolation reagent and oxidant. The selective mono- or di-sulfenylation could be controlled by addition of the amount of N-arylthiobenzamide. Excellent functional group tolerance was observed and thioethers or dithioethers were obtained in good yields. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.06.077

文献信息

• Copper-Catalyzed Aerobic Oxidative NS Bond Functionalization for CS Bond Formation: Regio- and Stereoselective Synthesis of Sulfones and Thioethers
  作者：Xianwei Li、Yanli Xu、Wanqing Wu、Chang Jiang、Chaorong Qi、Huanfeng Jiang

  DOI：10.1002/chem.201402815

  日期：2014.6.23

  A regio‐ and stereoselective synthesis of sulfones and thioethers by means of CuI‐catalyzed aerobic oxidative NS bond cleavage of sulfonyl hydrazides, followed by cross‐coupling reactions with alkenes and aromatic compounds to form the CS bond, is described herein. N2 and H2O are the byproducts of this transformation, thus offering an environmentally benign process with a wide range of potential

  本文描述了通过Cu I催化的磺酰肼的好氧氧化NS键裂解，随后与烯烃和芳族化合物的交叉偶联反应形成CS键的区域和立体选择性合成砜和硫醚的方法。。N 2和H 2 O是该转化过程的副产物，因此提供了一种环境友好的方法，在有机合成和药物化学中具有广泛的潜在应用。
• Rhodium-Catalyzed Directed Sulfenylation of Arene CH Bonds
  作者：Yaxi Yang、Wei Hou、Lihuai Qin、Juanjuan Du、Huijin Feng、Bing Zhou、Yuanchao Li

  DOI：10.1002/chem.201303730

  日期：2014.1.7

  The rhodium‐catalyzed intermolecular direct CH thiolation of arenes with aryl and alkyl disulfides was developed for the first time to provide a convenient route to aryl thioethers. This strategy is compatible with many different directing groups and exhibits excellent functional group tolerance. More significantly, mono‐ or dithiolation can be selectively achieved, thus providing a straightforward

  首次开发了铑催化芳烃和烷基二硫化物的分子间直接CH硫醇化反应，从而为制备芳基硫醚提供了便利的途径。该策略可与许多不同的导向基团兼容，并具有出色的官能团耐受性。更重要的是，可以选择性地实现单或二硫代化，从而为选择性制备芳基硫醚和二硫醚提供了直接的方法。
• Lewis Acid/Brønsted Acid Controlled Pd(II)-Catalyzed Chemodivergent Functionalization of C(<i>sp</i>²)–H Bonds with <i>N</i>-(Arylthio)i(a)mides
  作者：Manthena Chaitanya、Pazhamalai Anbarasan

  DOI：10.1021/acs.orglett.8b01281

  日期：2018.6.1

  C–H bonds have been accomplished employing N-(arylthio)imides in combination with either Brønsted acid or Lewis acid, respectively. Notable features of the developed methodologies include excellent diversity, high functional group tolerance, wide substrate scope, and use of a single N–S reagent. Importantly, the developed hypothesis was also successfully extended to the amidation of C–H bonds. A plausible

  使用N-（芳硫基）酰亚胺分别与Brønsted酸或Lewis酸结合使用，可实现高效的化学扩散的钯催化的硫键化（CS）和酰亚胺化（CN）。所开发方法的显着特征包括出色的多样性，高官能团耐受性，广泛的底物范围以及使用单个N-S试剂。重要的是，已发展的假设也成功地扩展到C–H键的酰胺化。在初步的机理研究的基础上，提出了一条可行的机理途径。
• Copper acetate - Iodine co-mediated thiolation of 2-arylpyridines with thiophenol
  作者：Yayun He、Senpeng Hou、Junhao Hu

  DOI：10.1016/j.tet.2021.132552

  日期：2022.1