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。
• Palladium-Catalyzed C–P(III) Bond Formation by Coupling ArBr/ArOTf with Acylphosphines
  作者：Xingyu Chen、Hongyu Wu、Rongrong Yu、Hong Zhu、Zhiqian Wang

  DOI：10.1021/acs.joc.1c00937

  日期：2021.7.2

  differential phosphination reagents is reported. The acylphosphines show practicable reactivity with ArBr and ArOTf as the phosphination reagents, though they are inert to the air and moisture. The reaction affords trivalent phosphines directly in good yields with a broad substrate scope and functional group tolerance. This reaction discloses the acylphosphines’ capability as new phosphorus sources for the direct

  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。
• Palladium(II) complexes of 2-, 3-, and 4-quinolinyl(diphenyl)phosphane and di-(3-quinolinyl)phenylphosphane: Synthesis, characterization, and catalytic screening
  作者：Juho Autio、Sauli Vuoti、M. Haukka、J. Pursiainen

  DOI：10.1016/j.ica.2007.09.009

  日期：2008.4

  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.