diethyl(o-phenylphenyl)phosphane | 1085850-83-4

• 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: diethyl(o-phenylphenyl)phosphane
• 英文别名: [1,1'-biphenyl-2-yl]diethylphosphine；Diethyl-(2-phenylphenyl)phosphane
• CAS: 1085850-83-4
• 化学式: C₁₆H₁₉P
• 分子量: 242.301
• InChiKey: ZDRIVGWQYUSLDJ-UHFFFAOYSA-N

物化性质

• 沸点：
  368.8±21.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 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：

  diethyl(o-phenylphenyl)phosphane 在 palladium(II) trifluoroacetate 、 双氧水 、 [双(三氟乙酰氧基)碘]苯 作用下， 以 甲醇 、 硝基甲烷 、 水 为溶剂， 反应 1.0h， 生成 2-(2-Diethylphosphorylphenyl)phenol
  参考文献：
  名称：

  Pd(II)-Catalyzed C(sp²)–H Hydroxylation with R₂(O)P-Coordinating Group

  摘要：

  A novel R-2(O)P-directed Pd(II)-catalyzed C-H hydroxylation to synthesize various substituted 2'-phosphorylbiphenyl-2-ol compounds is described. Notably, the reaction operates under mild conditions and shows good functional group tolerance, high selectivity, and yield.

  DOI：

  10.1021/ol403028a
• 作为产物：
  描述：

  苯硼酸 在 bis-triphenylphosphine-palladium(II) chloride 、 正丁基锂 、 potassium carbonate 作用下， 以 乙二醇二甲醚 、 乙醚 、 正己烷 、 水 为溶剂， 反应 8.0h， 生成 diethyl(o-phenylphenyl)phosphane
  参考文献：
  名称：

  Pd(II)-Catalyzed C(sp²)–H Hydroxylation with R₂(O)P-Coordinating Group

  摘要：

  A novel R-2(O)P-directed Pd(II)-catalyzed C-H hydroxylation to synthesize various substituted 2'-phosphorylbiphenyl-2-ol compounds is described. Notably, the reaction operates under mild conditions and shows good functional group tolerance, high selectivity, and yield.

  DOI：

  10.1021/ol403028a

文献信息

• Ir(III)-Catalyzed Direct C–H Functionalization of Arylphosphine Oxides: A Strategy for MOP-Type Ligands Synthesis
  作者：Zhong Liu、Ji-Qiang Wu、Shang-Dong Yang

  DOI：10.1021/acs.orglett.7b02710

  日期：2017.10.6

  efficiently applied to Ir(III)-catalyzed direct C–H functionalization of arylphosphine oxides. Involving C–H activation, carbene insertion, and tautomerism, this reaction proceeds under mild conditions, thus proving an approach to the synthesis of MOP-type ligand precursor in a single step. The utility of this transformation has been further demonstrated in ligand synthesis as well as in the construction

  重氮化合物作为偶联伙伴可有效地应用于Ir（III）催化的芳基膦氧化物的直接C–H官能化。涉及C–H活化，卡宾插入和互变异构，该反应在温和条件下进行，因此证明了一步合成MOP型配体前体的方法。这种转化的效用已在配体合成以及磷脂骨架的构建中得到了进一步证明。
• Palladium‐Catalyzed Suzuki–Miyaura Cross‐Coupling of Various Aryl Halides Using <i>ortho</i> ‐Alkyl‐Substituted Arylphosphanes and ( <i>ortho</i> ‐Alkylphenyl)alkylphosphanes under Microwave Heating
  作者：Sauli Vuoti、Juho Autio、Minna Laitila、Matti Haukka、Jouni Pursiainen

  DOI：10.1002/ejic.200700705

  日期：2008.1

  AbstractMono‐ and dinuclear palladium(II) chloride complexes of various ortho‐alkyl‐substituted aryl‐ and alkylphosphanes were prepared. Subsequently, these were characterized by 1H NMR and 31P1H} NMR spectroscopy, X‐ray crystallographic studies and mass spectroscopy. The palladium complexes were screened as potential catalysts for the microwave‐assisted Suzuki–Miyaura coupling reaction of several aryl halides under aerobic conditions. A preliminary study showed that excellent results can be obtained even for electron‐rich bromides and unactivated aryl chlorides with an optimized solvent, base and catalyst loading using specific phosphane ligands. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)
• Steric and Electronic Influences of Buchwald-Type Alkyl-JohnPhos Ligands
  作者：Alexander J. Kendall、Lev N. Zakharov、David R. Tyler

  DOI：10.1021/acs.inorgchem.5b02996

  日期：2016.3.21

  The electron-donating and steric properties of Buchwald-type ligands ([1,1'-biphenyl-2-yl]dialkylphosphine; R-JohnPhos, where R = Me, Et, Pr-i, Cy, Bu-t) were determined. The pi-acidity and sigma-donating properties of the R-JohnPhos ligands were quantified using a Cotton-Kraihanzel analysis of the Cr-0(CO)(5)(R-JohnPhos) complexes. Somewhat surprisingly, the sigma-donating abilities of the R-JohnPhos ligands follow the trend Bu-t-JohnPhos < Et-JohnPhos < Pr-i-JohnPhos < Cy-JohnPhos << Me-JohnPhos. This ordering is proposed to arise from competition between the intrinsic electron-donating ability of the R groups (Me < Et < Pr-i approximate to Cy < Bu-t) and steric interactions (front and back strain) that decrease the electron-donating ability of the phosphine. X-ray crystallographic data of 22 metal complexes (general forms: trans-Cr-0(CO)(4)(PR3)(2), Pd-0(PR3)(2)(eta(2)-dba), and trans-Pd-II(Cl)(2)(PR3)(2)) were also analyzed to help explain the electronic trends measured for the R-JohnPhos ligands. The R-JohnPhos ligands are exceptionally sensitive to back strain in comparison to typical phosphines, and the strong sigma-donating ability of the Methyl-JohnPhos ligand is attributed to its ability to avoid both front strain and back strain. Consequently, the -PMe2 moiety allows for very short phosphorus-metal bond distances. Because of the sterically dominating o-biphenyl and close phosphorus-metal bond distances, MeJPhos maintains a large overall steric profile that is actually larger than that of CyJPhos as measured by percent buried volume (%V-bur). Overall, the -PMe2 moiety is a powerful way to incorporate strong sigma-donation into designer phosphines while retaining other advantageous structural and reactivity properties.
• Effective new palladium catalysts for the Suzuki coupling of various haloxylenes to prepare sterically hindered bi- and triaryls
  作者：Sauli Vuoti、Juho Autio、M. Haukka、J. Pursiainen

  DOI：10.1016/j.ica.2009.06.032

  日期：2009.10

  Several new ortho-alkyl and heteroalkyl substituted aryl and aryl alkyl phosphanes and their palladium complexes have been selectively prepared, characterized and compared as potential catalysts for the Suzuki coupling reaction. The modification of the structures of the palladium complexes were made in search of the best possible catalytic activity. The novel catalysts were subsequently used to synthesize sterically hindered bi- and triaryls by coupling various bulky, unactivated bromoxylenes and chloroxylenes with a range of phenyl boronic acids under microwave irradiation. We showed that under optimized reaction conditions, very good results can be obtained with a selection of the new phosphanes and their mononuclear palladium complexes. (C) 2009 Elsevier B. V. All rights reserved.
• METAL COMPLEXES FOR USE IN THE CARBONYLATION OF ETHYLENICALLY UNSATURATED COMPOUNDS
  申请人：Lucite International UK Limited

  公开号：EP2007703A1

  公开（公告）日：2008-12-31