2-bromo-3-phenylbenzo[b]thiophene | 34281-44-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 英文名称: 2-bromo-3-phenylbenzo[b]thiophene
• 英文别名: 2-bromo-3-phenylbenzothiophene；2-Brom-3-phenyl-benzothiophen；2-Bromo-3-phenylbenzothiophen；2-Brom-3-phenyl-benzo[b]thiophen；2-bromo-3-phenyl-1-benzothiophene
• CAS: 34281-44-2
• 化学式: C₁₄H₉BrS
• 分子量: 289.195
• InChiKey: NHDAQXFEEAKFCF-UHFFFAOYSA-N

物化性质

• 沸点：
  400.3±33.0 °C(Predicted)
• 密度：
  1.486±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  28.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-bromo-3-phenylbenzo[b]thiophene 在 正丁基锂 、 N-氟代双苯磺酰胺 作用下， 以 乙醚 、 正己烷 、 四氢呋喃 为溶剂， 反应 2.5h， 以92%的产率得到2-fluoro-3-phenylbenzothiophene
  参考文献：
  名称：

  五元杂芳基溴化物的钯催化氟化深度评估

  摘要：

  A thorough investigation of the challenging Pd-catalyzed fluorination of five-membered heteroaryl bromides is presented. Crystallographic studies and density functional theory (DFT) calculations suggest that the challenging step of this transformation is C-F reductive elimination of five-membered heteroaryl fluorides from Pd(II) complexes. On the basis of these studies, we have found that various heteroaryl bromides bearing phenyl groups in the ortho position can be effectively fluorinated under catalytic conditions. Highly activated 2-bromoazoles, such as 8-bromocaffeine, are also viable substrates for this reaction.

  DOI：

  10.1021/acs.organomet.5b00631
• 作为产物：
  描述：

  3-溴苯并噻吩 在 potassium phosphate 、 N-溴代丁二酰亚胺(NBS) 、 甲烷磺酸(2-二环己基膦基-2',4',6'-三-异丙基-1,1'-联苯基)(2'-氨基-1,1'-联苯-2-基)钯(II) 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 2-bromo-3-phenylbenzo[b]thiophene
  参考文献：
  名称：

  五元杂芳基溴化物的钯催化氟化深度评估

  摘要：

  A thorough investigation of the challenging Pd-catalyzed fluorination of five-membered heteroaryl bromides is presented. Crystallographic studies and density functional theory (DFT) calculations suggest that the challenging step of this transformation is C-F reductive elimination of five-membered heteroaryl fluorides from Pd(II) complexes. On the basis of these studies, we have found that various heteroaryl bromides bearing phenyl groups in the ortho position can be effectively fluorinated under catalytic conditions. Highly activated 2-bromoazoles, such as 8-bromocaffeine, are also viable substrates for this reaction.

  DOI：

  10.1021/acs.organomet.5b00631

文献信息

• Bromide as the Directing Group for β-Arylation of Thiophenes
  作者：Hong-Hai Zhang、Cai-Xia Wang、Fei-Fei Sheng、Kai-Hui Liu、Jian-Guo Gu、Kang Shen、Zheng-Yi Sun、Kunlun Hong

  DOI：10.1055/a-1838-8958

  日期：2022.9

  Direct β-arylation of thiophene derivatives with bromide as directing group is disclosed. The reaction is conducted with PdCl2/(p-tolyl)3P as catalyst, silver carbonate as additive, and aryl iodide as coupling partner, affording brominated biaryl compounds as product. Control experiments indicated that the presence of bromide group enhances the reactivity of the C–H bond, enabling β-arylation. Furthermore

  公开了用溴化物作为导向基团的噻吩衍生物的直接β-芳基化。该反应以PdCl 2 /(对甲苯基) 3 P为催化剂，碳酸银为添加剂，芳基碘化物为偶联剂进行，得到溴代联芳基化合物作为产物。对照实验表明溴化物基团的存在增强了 C-H 键的反应性，使 β-芳基化成为可能。此外，C-Br 键可以通过多种方法轻松转化为许多有用的官能团。机理研究表明，银盐在 C-H 键活化步骤中起关键作用。
• Halocarbon chemistry. 3. Ortho metallation-induced cyclization of acetylenes: one-flask synthesis of 2,3-disubstituted benzofurans, thianaphthenes and indoles
  作者：Francis Johnson、Raghupathi Subramanian

  DOI：10.1021/jo00375a063

  日期：1986.12