2-(2-diphenylphosphinylphenyl)thiophene | 712350-53-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(2-diphenylphosphinylphenyl)thiophene
• 英文别名: 2-(2-Diphenylphosphorylphenyl)thiophene；2-(2-diphenylphosphorylphenyl)thiophene
• CAS: 712350-53-3
• 化学式: C₂₂H₁₇OPS
• 分子量: 360.416
• InChiKey: LISHWLAPSJLBAC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  45.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(2-diphenylphosphinylphenyl)thiophene 在 三氯硅烷 、 三乙胺 作用下， 以 甲苯 为溶剂， 以74%的产率得到2-(2'-{diphenylphosphino}phenyl)thiophene
  参考文献：
  名称：

  Palladium-catalysed synthesis of biaryl phosphines

  摘要：

  Monodentate, biphenyl-type phosphines have emerged as a powerful class of ligands in homogeneous catalysis. Synthetic methods for these ligands are limited, however. We report that the palladium-catalysed Suzuki coupling of OPR2(o-C6H4X) (R=Ph, t-Bu; X=Br, I) with arylboronic acids affords a variety of biaryl phosphine oxides including those that contain heterocycles. The corresponding phosphines are readily obtained by treatment with HSiCl3. The methodology provides an easy entry to monodentate biaryl and heterobiaryl P<^>X (X=N, O, S) phosphines with diverse steric and electronic properties. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.03.058
• 作为产物：
  描述：

  二苯基膦 在 palladium diacetate 、 bis(dibenzylideneacetone)-palladium⁽⁰⁾ potassium phosphate 、 双氧水 、 sodium acetate 、 三苯基膦 作用下， 以 1,4-二氧六环 、 甲醇 、 N,N-二甲基乙酰胺 为溶剂， 反应 121.0h， 生成 2-(2-diphenylphosphinylphenyl)thiophene
  参考文献：
  名称：

  Palladium-catalysed synthesis of biaryl phosphines

  摘要：

  Monodentate, biphenyl-type phosphines have emerged as a powerful class of ligands in homogeneous catalysis. Synthetic methods for these ligands are limited, however. We report that the palladium-catalysed Suzuki coupling of OPR2(o-C6H4X) (R=Ph, t-Bu; X=Br, I) with arylboronic acids affords a variety of biaryl phosphine oxides including those that contain heterocycles. The corresponding phosphines are readily obtained by treatment with HSiCl3. The methodology provides an easy entry to monodentate biaryl and heterobiaryl P<^>X (X=N, O, S) phosphines with diverse steric and electronic properties. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.03.058

文献信息

• P(O)R₂-Directed Enantioselective C–H Olefination toward Chiral Atropoisomeric Phosphine–Olefin Compounds
  作者：Shi-Xia Li、Yan-Na Ma、Shang-Dong Yang

  DOI：10.1021/acs.orglett.7b00608

  日期：2017.4.7

  An effective synthesis of chiral atropoisomeric biaryl phosphine-olefin compounds via palladium-catalyzed enantioselective C-H olefination has been developed for the first time. The reactions are operationally simple, tolerate wide functional groups, and have a good ee value, Notably, P(O)R-2 not only acts as the directing group to direct C-H activation in order to make a useful ligand but also serves to facilitate composition of the product in a useful manner in this transformation.