(N-phenyl-2-imidazolyl)diphenylphosphine | 566921-40-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (N-phenyl-2-imidazolyl)diphenylphosphine
• 英文别名: 2-(dicyclohexylphosphino)-1-phenyl-1H-imidazole；2-(diphenylphosphino)-1-phenyl-1H-imidazole；2-(diphenylphosphaneyl)-1-phenyl-1H-imidazole；1-benzyl-2-imidazolyldiphenylphosphine；2-(Diphenylphosphanyl)-1-phenyl-1H-imidazole；diphenyl-(1-phenylimidazol-2-yl)phosphane
• CAS: 566921-40-2
• 化学式: C₂₁H₁₇N₂P
• 分子量: 328.353
• InChiKey: MDZWLBXZTDYRJJ-UHFFFAOYSA-N

物化性质

• 熔点：
  124-125 °C
• 沸点：
  510.6±33.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  24
• 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：
  17.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (N-phenyl-2-imidazolyl)diphenylphosphine 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成
  参考文献：
  名称：

  碳稳定的氧化磷和硫化物

  摘要：

  碳→硫属o加合物，对应于目前为止由咪唑基亚烷基（NHC）和二氨基环丙烯基（BAC）供体提供的难以捉摸的游离氧代和硫代氧代磷鎓物种[R 2 P + = X]（X = O，S）的分子间稳定模式，已被隔离并具有完整特征。R 2 C：→P +（X）Ph 2键的位置特征是通过卡宾供体与氯离子的亲核取代以及NHC：→P +（O Ph 2与独立制备的BAC配体的加合物，从而得到BAC：→P +（O）Ph 2加合物。通过DFT计算得出，卡宾→硫属o体系对杂化解离模式的偏好优于均相解离模式。

  DOI：

  10.1002/chem.201202279
• 作为产物：
  描述：

  溴苯 在 copper(l) iodide 、 正丁基锂 、 四甲基乙二胺 、 potassium carbonate 作用下， 以 四氢呋喃 、 正己烷 、 二甲基亚砜 为溶剂， 反应 49.0h， 生成 (N-phenyl-2-imidazolyl)diphenylphosphine
  参考文献：
  名称：

  Effect of positive-charges in diphosphino-imidazolium salts on the structures of Ir-complexes and catalysis for hydroformylation

  摘要：

  The effect of positive charges in the diphosphino-imidazolium salts of L2 was investigated in terms of coordinating character, structures of corresponding Ir-complexes and catalysis for hydroformylation. It was found that the involved positive charges exhibited strong electron-withdrawing effect on the neighbored phosphine fragment, rendering L2 more pi-acceptor ability than the corresponding neutral counterpart of L1. Consequently, the changed coordinating ability of L1 and L2 led to the variety in the structures and components for the Ir-complexes (Ir-L1a, Ir-L1b, Ir-L2a, and Ir-L2b). The complexation of L2 with Ir(acac)(CO)(2) led to a novel five-coordinate Ir(II)-complex of Ir-L2a chelated by a PCC (phosphine-carboanion-carbene) pincer in tripodal mode, whereas the complexation of L1 with Ir(acac)(CO)(2) led to a four-coordinate square-planar KO-complex of Ir-L1a chelated by a PCP (phosphine-carboanion-phosphine) pincer. In addition, the different catalytic performances of these Ir-complexes ligated by L1 and L2 for hydroformylation of olefins were investigated. (C) 2015 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcata.2015.11.005
• 作为试剂：
  描述：

  苯胺 、 4-甲氧基苄醇 在 bis(1,5-cyclooctadiene)diiridium(I) dichloride 、 potassium tert-butylate 、 (N-phenyl-2-imidazolyl)diphenylphosphine 作用下， 以 二乙二醇二甲醚 为溶剂， 反应 4.0h， 以87%的产率得到N-苯基-4-甲氧基苄胺
  参考文献：
  名称：

  高效和可回收的Ir（I）催化剂，带有pi受体膦，可将芳胺与醇进行N-烷基化

  摘要：

  制备具有典型的α-受体特性的单膦（L1和L2）和二膦（L3和L4），并将其用于醇的Ir（I）催化胺的N-烷基化反应。发现...

  DOI：

  10.1039/c6gc03096c

文献信息

• Co-catalysis of a bi-functional ligand containing phosphine and Lewis acidic phosphonium for hydroformylation–acetalization of olefins
  作者：Yong-Qi Li、Peng Wang、Huan Liu、Yong Lu、Xiao-Li Zhao、Ye Liu

  DOI：10.1039/c5gc02127h

  日期：——

  L2 containing a phosphine and a Lewis acidic phosphonium exhibited synergetic catalysis and sequential catalysis for one-pot hydroformylation–acetalization.

  L2 包含一种膦和一种路易斯酸性磷酸铵，展示了协同催化和顺序催化，用于一锅法羰基化-缩醛化。
• Direct Amination of Bio-Alcohols Using Ammonia
  作者：Dennis Pingen、Olivier Diebolt、Dieter Vogt

  DOI：10.1002/cctc.201300407

  日期：2013.10

  A slightly adapted catalyst system has been successfully applied in the direct amination of primary and secondary alcohols. Moreover, the applicability to diols has been shown, giving high selectivity towards the primary diamines. It was found that the Ru/P ratio as well as the amount of ammonia used are highly important in this system, especially for higher substrate loadings. The catalyst was employed

  略有适应的催化剂体系已成功应用于伯醇和仲醇的直接胺化。而且，已经显示出对二醇的适用性，从而对伯二胺具有高选择性。发现Ru / P比以及所用氨的量在该系统中非常重要，特别是对于较高的底物负载。将该催化剂以较大的批量规模使用，以将异甘露聚糖转化为相应的二胺。另外，表明该催化剂在至少六个连续运行中是稳定的。没有观察到明显的活性和选择性损失。
• Monosubstituted, Anionic Imidazolyl Ligands from N−H NHC Precursors and Their Activity in Pd‐Catalyzed Cross‐Coupling Reactions
  作者：Erin E. Martinez、Christopher A. Jensen、Alexandra J. S. Larson、Karissa C. Kenney、Kyle J. Clark、S. Hadi Nazari、Gabriel A. Valdivia‐Berroeta、Stacey J. Smith、Daniel H. Ess、David J. Michaelis

  DOI：10.1002/adsc.202000483

  日期：2020.7.29

  We report that treatment of several 2‐diphenylphosphinoimidazoles with Pd(II) salts generates monosubstituted N−H NHC−Pd complexes via insertion into the C−P bond. Removal of the N−H proton in situ leads to anionic (X‐type) or imidazolyl‐Pd complexes that are highly stable and catalytically active, achieving up to 340,000 turnovers at 1 ppm catalyst loading in Suzuki‐Miyaura reactions. DFT‐calculated

  我们报告说，用Pd（II）盐处理几种2-diphenylphosphinoimidazoles会通过插入CP键生成单取代的NH NHC-Pd复合物。原位除去NH质子会生成高度稳定且具有催化活性的阴离子（X型）或咪唑基-Pd络合物，在Suzuki-Miyaura反应中，当催化剂负载1 ppm时，可实现高达340,000的周转率。DFT计算的空间小的配体的Tolman电子参数表明，这些配体比传统的NHC显着增加了供体，这为快速交叉偶联催化提供了理论依据。Sonogashira反应中也显示出优异的反应性。
• ——
  作者：M. N. Chevykalova、L. F. Manzhukova、N. V. Artemova、Yu. N. Luzikov、I. E. Nifant"ev、E. E. Nifant"ev

  DOI：10.1023/a:1022483912466

  日期：——

  The influence of aryl, heterocyclic, amide. alkyl, alkoxyl, thioalkoxyl, and ferrocenyl substituents at the phosphorus atom on its electron-donating ability was studied by the measurement of direct P-31-Se-77 spin-spin coupling constants for the corresponding selenides. Series of diphenylorganylphosphines and their selenides were studied.
• Synthesis, spectroscopic and structural characterization of novel adducts of some silver(I) salts with the ambidentate donor PPh2py
  作者：Augusto Cingolani、Effendy、Domenico Martini、Claudio Pettinari、Brian W. Skelton、Allan H. White

  DOI：10.1016/j.ica.2005.12.031

  日期：2006.4

  Syntheses, spectroscopic (R, H-1 and P-31 NMR) and some 'low'-temperature single-crystal X-ray structural characterizations are reported for a wide variety of adducts of AgX:PPh(2)py (:S) (n:m(:x)) (X = Cl, Br, I, NO2, SCN, ClO4, BF4, O2CCF3 (tfa), O2CCH3 (ac), O2CC3R7 (hefb), S2CN(C2H5)(2) (dtc), 1/2 SO42-; PPh(2)py = L = diphenyl-2-pyridylphosphine) stoichiometry. All compounds are binuclear, a wide range of (AgAg)-Ag-... distances being found, bridging entities being diverse, either anionic X or the P,N-ambidentate ligand PPh(2)py. PPh(2)py acts as a terminal P-donor in Agdtc: PPh(2)py (1:1)(2) and in [(Ph(2)py)(2)Ag([mu-Cl)(2)Ag(PPh(2)py)(NCMe)], but fully utilizes its coordinating capabilities in [(MeCN)Ag(mu-PPh(2)py)(3)Ag(OHI2)](ClO4)(2) and [(NO2)Ag(p-PPh(2)py)(2)Ag(O2N)]. Comparison is made between the latter compound and the analogous species [(NO2)Ag(mu-PPh(2)bim)(2)Ag(O2N)] (PPh(2)bim=L'=1-benzyl-2-imidazolyldiphenylphosphine). (c) 2005 Elsevier B.V. All rights reserved.