[1,1'-biphenyl]-4-yldiphenylphosphine | 13885-03-5

• 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: [1,1'-biphenyl]-4-yldiphenylphosphine
• 英文别名: 4-(diphenylphosphino) biphenyl；[1,1'-biphenyl]-4-yldiphenylphosphane；4,4'-(Diphenylphosphino)biphenyl；diphenyl-(4-phenylphenyl)phosphane
• CAS: 13885-03-5
• 化学式: C₂₄H₁₉P
• 分子量: 338.389
• InChiKey: BJRAEIPAPYZBMQ-UHFFFAOYSA-N

物化性质

• 熔点：
  84 °C
• 沸点：
  461.9±24.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 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：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  [1,1'-biphenyl]-4-yldiphenylphosphine 在 硫酸 、 sodium hydroxide 作用下， 以 水 为溶剂， 反应 72.0h， 以62%的产率得到Sodium;4-(4-diphenylphosphanylphenyl)benzenesulfonate
  参考文献：
  名称：

  新型易制备的两亲性膦在有机金属水溶液中的性质和催化活性

  摘要：

  三苯膦（PPh 3）和环己基（苯基）膦的单和二磺化两亲型很容易从商业试剂和硫酸中合成。通过表面张力，等温滴定量热法，核磁共振和低温透射电子显微镜研究了这些膦在溶液中的行为。根据磺化程度证明了两种不同的超分子组装。单磺化的膦形成了组织良好的胶束状聚集体，而二磺化的膦则形成了异质且无组织的囊状组装体。在两相，钯催化的烯丙基烷基碳酸酯的水相双相裂解中，评估了这些两亲膦的效率。

  DOI：

  10.1002/adsc.201000014
• 作为产物：
  描述：

  4,4'-二溴联苯 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 3.0h， 生成 [1,1'-biphenyl]-4-yldiphenylphosphine
  参考文献：
  名称：

  An examination of the effects of borate group proximity on phosphine donor power in anionic (phosphino)tetraphenylborate ligands

  摘要：

  The ligand electron-donating abilities are compared among a series of monodentate, anionic (phosphino) tetraphenylborate phosphines [Ph4P][Ph2P-R-C6H4BPh3] (R = -C6H4-, -CH2-, -CH2CH2- or none), and their neutral counterparts Ph2PR (R = biphenyl, -CH2Ph, -CH2CH2Ph or Ph). Among the anionic ligands, the position of the tetraphenylborate group relative to the diphenylphosphino donor moiety was systematically varied in an effort to examine how its proximity impacts donor power. The donor power was determined by measuring the (3)1P-Se-77 coupling constant for the corresponding selenide of each phosphine ligand via P-31 NMR spectroscopy. The anionic ligands yield lower P-31-Se-77 coupling constants than those measured for their respective neutral counterparts. Moreover, the P-31-Se-77 coupling constants among the anionic ligands increase when the tetraphenylborate group is positioned further from the phosphorus centre. (C) 2014 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2014.10.048

文献信息

• Diverse C–P Cross-Couplings of Arylsulfonium Salts with Diarylphosphines via Selective C–S Bond Cleavage
  作者：Yun Ye、Jie Zhu、Yinhua Huang

  DOI：10.1021/acs.orglett.1c00748

  日期：2021.3.19

  Diverse C–P cross-couplings of arylthianthrenium salts with diarylphosphines producing various triarylphosphines via highly selective C–S bond cleavage are reported. In the absence of catalyst, the reaction of arylthianthrenium salts with diarylphosphines undergoes phosphinative ring opening exclusively via the cleavage of an endocyclic C–S bond of a thianthrene skeleton. The use of a palladacycle

  据报道，芳基噻吨鎓盐与二芳基膦通过不同的C–P交叉偶联，可通过高选择性的C–S键裂解产生各种三芳基膦。在没有催化剂的情况下，芳基噻吨鎓盐与二芳基膦的反应仅通过裂解噻吩骨架的内环C–S键进行膦化开环。在其他条件相同的情况下使用Palladacycle催化剂，则可以通过裂解环外C-S键以更高的速度进行磷酸化反应。
• 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。
• A practical synthesis of unsymmetrical triarylphosphines by heterogeneous palladium(0)-catalyzed cross-coupling of aryl iodides with diphenylphosphine
  作者：Zhaotao Xu、Pingping Wang、Qiurong Chen、Mingzhong Cai

  DOI：10.1016/j.jorganchem.2018.04.018

  日期：2018.7

  The heterogeneous cross-coupling reaction of aryl iodides with diphenylphosphine was achieved in DMAc at 130 °C in the presence of 1.0 mol% of MCM-41-supported tridentate nitrogen palladium(0) complex [MCM-41-3N-Pd(0)] with KOAc as base, yielding a variety of unsymmetrical triarylphosphines in good to excellent yields. The turnover frequency (TOF) of the catalyst can reach 30.67 h−1. This new heterogeneous

  在1.0 mol％MCM-41负载的三齿氮钯（0）络合物[MCM-41-3N-Pd（0）用KOAc作为碱，可产生各种不对称的三芳基膦，收率良好至极佳。催化剂的周转频率（TOF）可以达到30.67h -1。这种新的多相钯（0）催化剂可以通过简单的方法轻松地从市售试剂中制备，并显示出与均相Pd（OAc）2或Pd（PPh 3）4相同的催化活性。可以通过过滤反应溶液进行回收，并循环至少七次而不会显着降低催化活性。
• An efficient heterogeneous cross-coupling of aryl iodides with diphenylphosphine catalyzed by copper (I) immobilized in MCM-41
  作者：Zhiqiang Fang、Mingzhong Cai、Yang Lin、Hong Zhao

  DOI：10.1002/aoc.4417

  日期：2018.8

  The heterogeneous cross‐coupling reaction of aryl iodides with diphenylphosphine was achieved in toluene at 115 °C in the presence of 10 mol% of phenanthroline‐functionalized MCM‐41‐supported copper (I) complex (Phen‐MCM‐41‐CuI) with Cs2CO3 as base, yielding various unsymmetric triarylphosphines in good to excellent yields. This protocol can tolerate a wide range of functional groups and does not need

  在10 mol％的邻菲咯啉官能化的MCM-41-负载的铜（I）络合物（Phen-MCM-41-CuI）和10 mol％的存在下，芳基碘化物与二苯膦的异质交叉偶联反应在115°C的甲苯中完成以Cs 2 CO 3为碱，以良好或优异的产率产生各种不对称的三芳基膦。该方案可以耐受各种官能团，不需要使用昂贵的添加剂或苛刻的反应条件。这种非均相的Cu（I）催化剂具有与均相CuI / Phen系统相同的催化活性，可以通过简单过滤反应溶液轻松回收，并循环使用七次而不会显着降低活性。
• Palladium-catalyzed C–P(III) bond formation reaction with acylphosphines as phosphorus source
  作者：Rongrong Yu、Xingyu Chen、Zhiqian Wang

  DOI：10.1016/j.tetlet.2016.06.088

  日期：2016.7

  Palladium-catalyzed C–P(III) bond formation reaction employing acylphosphines as the phosphorus source was developed. Under the optimized conditions, acylphosphines could react with aryl halides directly affording trivalent phosphines in up to 94% yield.

  开发了以酰基膦为磷源的钯催化的C-P（III）键形成反应。在最佳条件下，酰基膦可以与芳基卤化物直接反应，从而以高达94％的收率获得三价膦。