2-(diphenylphosphino)-N-phenylaniline | 5727-68-4

• 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-(diphenylphosphino)-N-phenylaniline
• 英文别名: 2-diphenylphosphanyl-N-phenylaniline
• CAS: 5727-68-4
• 化学式: C₂₄H₂₀NP
• 分子量: 353.403
• InChiKey: MZYVNRHFOZMNQR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-(diphenylphosphino)-N-phenylaniline 在 六氟磷酸银 、 lithium 、 potassium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 72.0h， 生成 [(PhNP)Cu (PMe3)2]2
  参考文献：
  名称：

  Noninnocent Behavior of Bidentate Amidophosphido [NP]^2– Ligands upon Coordination to Copper

  摘要：

  The synthesis and preliminary coordination chemistry of two new redox-active bidentate ligands containing amido and phosphido donors are described. Treatment of the [(NP)-N-R](2-) (R = Ph, 2,4,6-trimethylphenyl) ligands with CuCl2 and PMe3 results in a dimeric copper(I) P-P coupled product via ligand oxidation. The intermediate of this reaction is proposed to involve a ligand radical generated via oxidation of the [(NP)-N-R](2-) ligand by copper(II), and the existence of such an intermediate is probed using computational methods. Significant radical character on the phosphorus atoms of the alleged [(NP)-N-R](center dot-)/copper(I) intermediate leads to P-P radical coupling.

  DOI：

  10.1021/ic402257z
• 作为产物：
  描述：

  2-氟苯胺 在 1,1'-双(二苯基膦)二茂铁 、 tris-(dibenzylideneacetone)dipalladium(0) 、 sodium t-butanolate 作用下， 以 1,4-二氧六环 为溶剂， 反应 48.0h， 生成 2-(diphenylphosphino)-N-phenylaniline
  参考文献：
  名称：

  Noninnocent Behavior of Bidentate Amidophosphido [NP]^2– Ligands upon Coordination to Copper

  摘要：

  The synthesis and preliminary coordination chemistry of two new redox-active bidentate ligands containing amido and phosphido donors are described. Treatment of the [(NP)-N-R](2-) (R = Ph, 2,4,6-trimethylphenyl) ligands with CuCl2 and PMe3 results in a dimeric copper(I) P-P coupled product via ligand oxidation. The intermediate of this reaction is proposed to involve a ligand radical generated via oxidation of the [(NP)-N-R](2-) ligand by copper(II), and the existence of such an intermediate is probed using computational methods. Significant radical character on the phosphorus atoms of the alleged [(NP)-N-R](center dot-)/copper(I) intermediate leads to P-P radical coupling.

  DOI：

  10.1021/ic402257z
• 作为试剂：
  描述：

  亚磷酸三乙酯 、 2,7-dibromospiro[fluorene-9,9'-xanthene] 在 2-(diphenylphosphino)-N-phenylaniline 、 sodium t-butanolate 作用下， 以 二甲基亚砜 为溶剂， 以82 %的产率得到
  参考文献：
  名称：

  一种界面修饰层材料及应用该材料的钙钛矿太阳能电池

  摘要：

  本发明公开了一种界面修饰层材料及应用该材料的钙钛矿太阳能电池，属于钙钛矿太阳能电池领域，设计了一系列以螺环为主体带有不同数目、不同种类路易斯碱基团的界面修饰材料，通过引入路易斯碱基团钝化钙钛矿中能形成深能级陷阱的缺陷，螺环主体和经典空穴传输材料形成激基复合物，目的是解决现有的经典空穴传输材料与钙钛矿层接触不紧密造成的载流子传输损失问题，此外，本发明还涉及采用前述界面修饰材料制备的钙钛矿太阳能电池。本发明的有益效果在于：界面修饰材料的独特结构设计可以钝化钙钛矿膜表面缺陷，同时促进钙钛矿层与经典空穴传输层之间的载流子传输，提升了钙钛矿太阳能电池的器件效率和稳定性。

  公开号：

  CN117586301A

文献信息

• Highly Regio- and Enantioselective Hydroformylation of Vinyl Esters Using Bidentate Phosphine,P-Chiral Phosphorodiamidite Ligands
  作者：Christian Schmitz、Katharina Holthusen、Walter Leitner、Giancarlo Franciò

  DOI：10.1021/acscatal.5b02846

  日期：2016.3.4

  Very high enantioselectivities of up to 97% ee accompanied by excellent regioselectivities (up to b/l > 1000) were obtained using the BettiPhos ligand (SC,SC,RP,SC)-4b bearing an additional chiral group at the aniline nitrogen. The catalyst resting state [RhH(CO)2(SC,SC,RP,SC)-4b}] was investigated by high pressure-NMR studies, revealing an equatorial–apical coordination of the bidentate ligand where

  已经制备了基于手性贝蒂碱骨架和二苯基膦基苯胺衍生物的混合二齿膦-亚磷酰胺基配体（BettiPhos）。配体在亚磷酰胺基部分具有立体异构的P原子，其构型可在很大程度上由合成途径以及碱和溶剂的选择控制。新的配体用于乙烯基酯和乙烯基酰胺的铑催化的不对称加氢甲酰化（AHF）。使用BettiPhos配体（S C，S C，R P，S C）-4b获得了高达97％ee的极高对映选择性和极佳的区域选择性（高达b / l> 1000）在苯胺氮上带有一个额外的手性基团。通过高压NMR研究了催化剂的静止状态[RhH（CO）2 （S C，S C，R P，S C）-4b }]，揭示了双齿配体的赤道-顶峰配位，其中两个磷供体通过中间体与仅通过膦基结合的配体快速交换位置。
• Insertion of Arynes into Arylphosphoryl Amide Bonds: One-Step Simultaneous Construction of C–N and C–P Bonds
  作者：Chaoren Shen、Guoqiang Yang、Wanbin Zhang

  DOI：10.1021/ol402748u

  日期：2013.11.15

  The insertion of arynes into arylphosphoryl amide bonds to synchronously construct C-P and C-N bonds is described. Arynes generated in situ from o-triflate arylsilanes under fluoride-promoted conditions insert into relatively inert P-N bonds, producing o-amine-substituted arylphosphine oxides. This process provides a simple pathway for the preparation of precursors for a number of bidentate aminophosphine ligands.
• Tunable Hemilabile Ligands for Adaptive Transition Metal Complexes
  作者：Ronald Lindner、Bart van den Bosch、Martin Lutz、Joost N. H. Reek、Jarl Ivar van der Vlugt

  DOI：10.1021/om100804k

  日期：2011.2.14

  A new family of monoanionic hemilabile ligands L1H-L3H with a PNN donor set has been developed, based on Pd-catalyzed C-N bond formation and straightforward phosphorylation. For these structurally related compounds with a hybrid set of donor atoms, the coordination chemistry with both Rh and Ir has been studied. The anticipated hemilabile character of the dimethylamino group was assessed by NMR and IR competition experiments, using isopropyl isocyanide as exogenous substrate. Supporting DFT calculations were used to quantify the electronic differences between the various members of the ligand family. In effect, we have constructed a modular ligand class that exhibits tunable hemilability.
• Highly Efficient and Versatile Phosphine-Phosphoramidite Ligands for Asymmetric Hydrogenation
  作者：Matthias Eggenstein、Anika Thomas、Jens Theuerkauf、Giancarlo Franciò、Walter Leitner

  DOI：10.1002/adsc.200800653

  日期：2009.3

  Abstractmagnified imageA set of novel phosphine‐phosphoramidite ligands possessing two elements of chirality have been prepared through a modular synthetic approach. The ligands (11bS)‐N‐[2‐(diphenylphosphino)phenyl]‐N‐[(S)‐1‐phenylethyl]dinaphtho[2,1‐d:1′,2′‐f][1,3,2]dioxaphosphepin‐4‐amine [(Sa,Sc)‐1a] and (11bR)‐N‐[2‐(diphenylphosphino)phenyl]‐N‐[(S)‐1‐(1‐naphthyl)ethyl]dinaphtho[2,1‐d:1′,2′‐f][1,3,2]dioxaphosphepin‐4‐amine [(Sa,Sc)‐1b] are unique in providing enantioselectivities ≥96% ee and ≥94% ee, respectively, in mechanistically distinct hydrogenations of CC, CN and CO double bonds in combination with three different transition metals (rhodium, iridium, and ruthenium, respectively). Particularly remarkable are the enantiomeric excesses up to 97% achieved in the iridium‐catalyzed hydrogenation of 2‐substituted quinolines, where (11bS)‐N‐[2‐(diphenylphosphino)phenyl]‐N‐[(S)‐1‐(naphthalen‐1‐yl)ethyl]‐8,9,10,11, 12,13,14,15‐octahydrodinaphtho[2,1‐d:1′,2′‐f][1,3,2]dioxaphosphepin‐4‐amine [(Sa,Sc)‐2] proved to be the most selective ligand. Substantially lower ees were obtained with the mismatched diastereomer (Ra,Sc)‐1b and with the N‐phenyl‐substituted ligand 1c, missing a second element of chirality.