N-(sec-butyl)benzo[b]thiophen-5-amine

• 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: N-(sec-butyl)benzo[b]thiophen-5-amine
• 英文别名: N-butan-2-yl-1-benzothiophen-5-amine
• 化学式: C₁₂H₁₅NS
• 分子量: 205.324
• InChiKey: PYWMEBCJBDADPJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  40.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  5-氯苯并噻吩 、 仲丁胺 在 C₂₉H₃₂O₄P₂*C₇H₇^(1-)*Ni⁽²⁺⁾*Cl^(1-) 、 sodium t-butanolate 作用下， 以 甲苯 为溶剂， 反应 16.0h， 以61%的产率得到N-(sec-butyl)benzo[b]thiophen-5-amine
  参考文献：
  名称：

  某些重要的双膦镍（II）预催化剂在C–N交叉偶联中的比较反应性研究

  摘要：

  The synthesis and characterization of the new air-stable precatalyst (L1)Ni(o-tol)Cl (Cl; where L1 = JosiPhos CyPF-Cy) is reported, along with the results of a comparative reactivity survey involving Cl and analogous PAd-DalPhos- and DPPF-containing precatalysts (C2 and C3, respectively) in representative nickel-catalyzed C(sp(2))-N cross-coupling reactions. Precatalyst C1 was found to be competitive with, and in some cases complementary to, C2 in the monoarylation of ammonia and primary alkylamines with (hetero)aryl chlorides, including in otherwise challenging room temperature transformations. (Pseudo)halide comparison studies involving the cross-coupling of furfurylamine at room temperature revealed that in contrast to C2 precatalyst Cl performs less effectively with aryl bromides. Whereas C3 was found to be ineffective for such transformations, this DPPF-derived precatalyst proved superior to C1 and C2 in reactions involving the secondary dialkylamine test substrate morpholine.

  DOI：

  10.1021/acs.organomet.6b00650

文献信息

• A Comparative Reactivity Survey of Some Prominent Bisphosphine Nickel(II) Precatalysts in C–N Cross-Coupling
  作者：Jillian S. K. Clark、Christopher M. Lavoie、Preston M. MacQueen、Michael J. Ferguson、Mark Stradiotto

  DOI：10.1021/acs.organomet.6b00650

  日期：2016.9.26

  The synthesis and characterization of the new air-stable precatalyst (L1)Ni(o-tol)Cl (Cl; where L1 = JosiPhos CyPF-Cy) is reported, along with the results of a comparative reactivity survey involving Cl and analogous PAd-DalPhos- and DPPF-containing precatalysts (C2 and C3, respectively) in representative nickel-catalyzed C(sp(2))-N cross-coupling reactions. Precatalyst C1 was found to be competitive with, and in some cases complementary to, C2 in the monoarylation of ammonia and primary alkylamines with (hetero)aryl chlorides, including in otherwise challenging room temperature transformations. (Pseudo)halide comparison studies involving the cross-coupling of furfurylamine at room temperature revealed that in contrast to C2 precatalyst Cl performs less effectively with aryl bromides. Whereas C3 was found to be ineffective for such transformations, this DPPF-derived precatalyst proved superior to C1 and C2 in reactions involving the secondary dialkylamine test substrate morpholine.