5-(p-acetylphenyl)-2,2'-bithiophene

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-(p-acetylphenyl)-2,2'-bithiophene
• 英文别名: 1-(4-[2,2'-Bithiophen]-5-ylphenyl)ethanone；1-[4-(5-thiophen-2-ylthiophen-2-yl)phenyl]ethanone
• 化学式: C₁₆H₁₂OS₂
• 分子量: 284.403
• InChiKey: QEPJVKTUYUTITR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  19
• 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：
  73.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-碘代苯乙酮 、 2,2'-联二噻吩 在 RhCl(CO){P[OCH(CF₃)₂]₃}₂ 乙二醇二甲醚 、 silver carbonate 作用下， 以 xylene 为溶剂， 反应 0.5h， 以64%的产率得到5-(p-acetylphenyl)-2,2'-bithiophene
  参考文献：
  名称：

  Direct C−H Arylation of (Hetero)arenes with Aryl Iodides via Rhodium Catalysis

  摘要：

  A new method for the catalytic C-H arylation of heteroarenes and arenes that manifests high activity paired with reasonably broad scope was developed. Under the catalytic influence of RhCl(CO){P[OCH(CF3)2]3}2 and Ag2CO3, the direct C-H arylation of heteroarenes/arenes with aryl/heteroaryl iodides took place to afford a range of biaryls in good to excellent yields with high regioselectivity. Thiophenes, furans, pyrroles, indoles, and alkoxybenzenes are applicable in this arylation protocol.

  DOI：

  10.1021/ja064500p

文献信息

• Palladium‐Catalysed Direct Monoarylation of Bithiophenyl Derivatives or Bis(thiophen‐2‐yl)methanone with Aryl Bromides
  作者：Karima Si Larbi、Safia Djebbar、Henri Doucet

  DOI：10.1002/ejic.201100294

  日期：2011.8

  Arylated bithiophenes, which are useful compounds due to their coordination and/or physical properties, can be easily prepared by palladium-catalysed C–H bond activation of heteroaromatics followed by arylation using electron-deficient aryl bromides. A variety of 5-arylated 2,2′-bithiophenyl derivatives have been prepared. Good yields were generally obtained by using the air-stable [PdCl(dppb)(C3H5)]

  芳基化联噻吩由于其配位和/或物理性质而成为有用的化合物，可以通过钯催化的杂芳烃的 C-H 键活化，然后使用缺电子的芳基溴化物进行芳基化来轻松制备。已经制备了多种 5-芳基化 2,2'-联噻吩衍生物。通过使用空气稳定的 [PdCl(dppb)(C3H5)] 配合物作为催化剂，通常可以获得良好的产率。芳基溴上的一系列官能团，例如乙酰基、甲酰基、酯、腈、三氟甲基、氟和羟烷基，是可以容忍的。
• Direct C−H Arylation of (Hetero)arenes with Aryl Iodides via Rhodium Catalysis
  作者：Shuichi Yanagisawa、Tomoko Sudo、Ryoji Noyori、Kenichiro Itami

  DOI：10.1021/ja064500p

  日期：2006.9.1

  A new method for the catalytic C-H arylation of heteroarenes and arenes that manifests high activity paired with reasonably broad scope was developed. Under the catalytic influence of RhCl(CO)P[OCH(CF3)2]3}2 and Ag2CO3, the direct C-H arylation of heteroarenes/arenes with aryl/heteroaryl iodides took place to afford a range of biaryls in good to excellent yields with high regioselectivity. Thiophenes, furans, pyrroles, indoles, and alkoxybenzenes are applicable in this arylation protocol.
• Direct coupling of arenes and iodoarenes catalyzed by a rhodium complex with a strongly π-accepting phosphite ligand
  作者：Shuichi Yanagisawa、Tomoko Sudo、Ryoji Noyori、Kenichiro Itami

  DOI：10.1016/j.tet.2008.01.053

  日期：2008.6

  A new rhodium-based catalytic system for the direct C-H coupling of arenes and iodoarenes that shows high activity with reasonably broad scope was developed. Under the catalytic influence of RhCl(CO)P[OCH(CF3)(2)](3)}(2) and Ag2CO3, the direct C-H arylation of heteroarenes and arenes took place with iodoarenes to afford a range of biaryls in good to excellent yields with high regioselectivity. Thiophenes, furans, pyrroles, indoles, and alkoxybenzenes are applicable to this arylation protocol. (C) 2008 Elsevier Ltd. All rights reserved.