2-(1,2-diphenylethyl)thiophene

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 2-(1,2-diphenylethyl)thiophene
• 英文别名: 2-(1,2-Diphenylethyl)thiophene
• 化学式: C₁₈H₁₆S
• 分子量: 264.391
• InChiKey: NJWLHSINTBDWND-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  28.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2-苯甲酰噻吩 在 正丁基锂 、 1,10-菲罗啉 、 sodium hydride 作用下， 以 四氢呋喃 、 正己烷 、 苯 为溶剂， 反应 19.0h， 生成 2-(1,2-diphenylethyl)thiophene
  参考文献：
  名称：

  Transition‐Metal‐Free Intermolecular Hydrocarbonation of Styrenes Mediated by NaH/1,10‐Phenanthroline

  摘要：

  AbstractA transition‐metal‐free intermolecular coupling reaction of halocompounds with styrenes in the presence of NaH and 1,10‐phenanthroline was developed. This reaction afforded hydrocarbonated products with complete anti‐Markovnikov selectivity. The method allows the use of a wide range of halocompounds, including aryl and alkyl halides, and good functional group tolerance. Detailed mechanistic studies indicated that an anilide anion generated in situ by the NaH‐mediated reduction of 1,10‐phenanthroline works as an electron donor and a hydrogen source.

  DOI：

  10.1002/chem.202203143

文献信息

• 10.1039/d4sc04011b
  作者：Assani, Nadhrata、Delfau, Ludivine、Smits, Preslav、Redon, Sebastien、Kabri, Youssef、Tomas-Mendivil, Eder、Vanelle, Patrice、Martin, David、Broggi, Julie

  DOI：10.1039/d4sc04011b

  日期：——

  Catalytic amounts of 1,3-di(methyl)imidazole-2-ylidene, one of the simplest and most prototypical N-heterocyclic carbenes, can up-convert aldehydes into powerful stoichiometric sources of electrons (Super Electron Donors) for reductive transformations of iodoaryls (Ered < −2 V). In particular, the hydroarylation of 1,1′-diarylethylenes, which may require high temperatures and inherently generate stoichiometric

  催化量的 1,3-二（甲基）咪唑-2-亚基（最简单和最具原型的 N-杂环卡宾之一）可以将醛上转换为强大的化学计量电子源（超级电子供体），用于碘芳基的还原转化（ E红色< −2 V）。特别是，1,1'-二芳基乙烯的加氢芳基化可能需要高温并固有地产生化学计量量的氧化废物，但在室温下进行，同时形成作为氧化副产物的酯。
• Transition‐Metal‐Free Intermolecular Hydrocarbonation of Styrenes Mediated by NaH/1,10‐Phenanthroline
  作者：Kanako Nozawa‐Kumada、So Onuma、Kanako Ono、Tomohiro Kumagai、Yuki Iwakawa、Katsuhiko Sato、Masanori Shigeno、Yoshinori Kondo

  DOI：10.1002/chem.202203143

  日期：2023.3.28

  AbstractA transition‐metal‐free intermolecular coupling reaction of halocompounds with styrenes in the presence of NaH and 1,10‐phenanthroline was developed. This reaction afforded hydrocarbonated products with complete anti‐Markovnikov selectivity. The method allows the use of a wide range of halocompounds, including aryl and alkyl halides, and good functional group tolerance. Detailed mechanistic studies indicated that an anilide anion generated in situ by the NaH‐mediated reduction of 1,10‐phenanthroline works as an electron donor and a hydrogen source.