4-(diphenylphosphanyl)quinoline | 1021148-69-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 4-(diphenylphosphanyl)quinoline
• 英文别名: 4-diphenylphosphanequinoline；Diphenyl(quinolin-4-yl)phosphane；diphenyl(quinolin-4-yl)phosphane
• CAS: 1021148-69-5
• 化学式: C₂₁H₁₆NP
• 分子量: 313.339
• InChiKey: ULZHJSRIOCQUOV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  dichloro(cycloocta-1,5-diene)palladium (II) 、 4-(diphenylphosphanyl)quinoline 以 乙醚 为溶剂， 以62.3%的产率得到dichlorobis(4-diphenylphosphanequinoline)palladium(II)
  参考文献：
  名称：

  Palladium(II) complexes of 2-, 3-, and 4-quinolinyl(diphenyl)phosphane and di-(3-quinolinyl)phenylphosphane: Synthesis, characterization, and catalytic screening

  摘要：

  One previously known and three novel quinolinyl phosphanes were synthesized by either a reaction between a lithiated diphenylphosphane and the appropriate chloroquinoline or by a reaction between a lithiated haloquinoline and an arylchlorophosphane. The reaction of the quinolinyl phenylphosphane ligands with PdCl2(cod) produced monomeric palladium complexes in diethyl ether and dimeric, chlorine-bridged complexes in dichloromethane. Crystal structures of the palladium complexes confirm that the quinolinyl phenylphosphanes do not form chelated structures while bonded to the metal centre. 2-Quinolinyl(diphenyl) phosphane has a tendency to form a cis-isomer while bonded to the metal centre in the mononuclear complex due to attractive interactions between two ligands. A catalytic study showed that the quinolinyl phenylphosphane ligands are moderately active in the Suzuki-Miyaura coupling of various aryl halides in air. (C) 2007 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ica.2007.09.009
• 作为产物：
  描述：

  二苯基膦 在 [1,3-双(二苯基膦基)丙烷]二氯化钯(II) 、 caesium carbonate 、 三乙胺 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 18.0h， 生成 4-(diphenylphosphanyl)quinoline
  参考文献：
  名称：

  通过将 ArBr/ArOTf 与酰基膦偶联形成钯催化的 C-P(III) 键

  摘要：

  据报道，钯催化的 ArBr/ArOTf 的 C-P 键形成反应使用酰基膦作为差异膦化试剂。酰基膦显示出与作为膦化试剂的 ArBr 和 ArOTf 的实际反应性，尽管它们对空气和湿气呈惰性。该反应直接以良好的收率提供三价膦，具有广泛的底物范围和官能团耐受性。该反应揭示了酰基膦作为直接合成三价膦的新磷源的能力。

  DOI：

  10.1021/acs.joc.1c00937

文献信息

• Ru^(II)-catalyzed P^(III)-assisted C8-alkylation of naphthphosphines
  作者：Wen-Tao Ma、Mao-Gui Huang、Yueliuting Fu、Zhong-Hui Wang、Jun-Yang Tao、Jia-Wei Li、Yue-Jin Liu、Ming-Hua Zeng

  DOI：10.1039/d2cc02161g

  日期：——

  We report a phosphine-directed ruthenium-catalyzed C8-selective alkylation of naphthalenes with alkenes. This protocol provides straightforward access to a large library of electron-rich C8-alkyl substituent 1-naphthphosphines, which outperformed common commercial phosphines and their precursors in the Pd-catalyzed Suzuki–Miyaura coupling of aryl bromides with alkylboronic acid.

  我们报告了萘与烯烃的膦定向钌催化的 C8 选择性烷基化。该协议提供了对富含电子的 C8-烷基取代基 1-萘膦的大型库的直接访问，该库在芳基溴化物与烷基硼酸的 Pd 催化 Suzuki-Miyaura 偶联中优于常见的商业膦及其前体。