di-tert-butyl(phenylethynyl)phosphine oxide | 870074-39-8

• 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: di-tert-butyl(phenylethynyl)phosphine oxide
• 英文别名: 2-Ditert-butylphosphorylethynylbenzene；2-ditert-butylphosphorylethynylbenzene
• CAS: 870074-39-8
• 化学式: C₁₆H₂₃OP
• 分子量: 262.332
• InChiKey: XTGULINADIOQLD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  Co2(CO)4(μ-CO)2(μ-bis(diphenylphosphino)methane) 、 di-tert-butyl(phenylethynyl)phosphine oxide 以 甲苯 为溶剂， 以94%的产率得到[(μ-bis(diphenylphosphino)methane)Co2(CO)4][μ,η-PhCCP(O)(t-Bu)2]
  参考文献：
  名称：

  Design, Synthesis, Application, and DFT Investigation of Suzuki−Miyaura Reactions of a Dicobalt Carbonyl-Containing Phosphine Ligand

  摘要：

  The preparation and characterization of a novel dicobalt-containing monophosphine ligand, 4a, is presented. Palladium-catalyzed Suzuki-Miyuara reactions employing 4a/Pd(OAc)(2) were pursued. The optimized reaction conditions were found to start with 1 molar equiv of aryllialides, 1.5-fold of phenylbronic acid, 3-fold of KF in 1 mL of THF, and I mol % of 4a/Pd(OAc)2 as catalytic precursor. The P-31 NMR studies reveal moderate reductive capacity of 4a toward Pd(OAc)(2). The unique bonding mode of 4a toward Pd ensures that the ratio of 4a/Pd is equal to 1:1. Two plausible active species, I and [I-OAc](-), were proposed as the catalytically active species in the Suzuki-Miyaura cross-coupling reaction. The validity of this assumption was examined by P-31 NMR spectra and density functional theory (DFT) means. In addition, we have demonstrated theoretically that the dicobalt moiety of 4a acts as an effective auxiliary in stabilizing the Pd(0) center during catalytic reaction.

  DOI：

  10.1021/om050060j

文献信息

• Synthesis of 2-Indolylphosphines by Palladium-Catalyzed Annulation of 1-Alkynylphosphine Sulfides with 2-Iodoanilines
  作者：Azusa Kondoh、Hideki Yorimitsu、Koichiro Oshima

  DOI：10.1021/ol1001544

  日期：2010.4.2

  Palladium-catalyzed annulation of 1-alkynylphosphine sulfides with 2-iodoanilines followed by desulfidation affords 3-substituted 2-indolylphosphines. This annulation/desulfidation sequential protocol offers a conceptually new approach to bulky heteroarylphosphines.

  钯催化的1-炔基膦硫化物与2-碘苯胺的环化，然后进行脱硫，得到3-取代的2-吲哚基膦。这种环化/脱硫顺序方案为大体积的杂芳基膦提供了一种概念上新的方法。
• Design, Synthesis, Application, and DFT Investigation of Suzuki−Miyaura Reactions of a Dicobalt Carbonyl-Containing Phosphine Ligand
  作者：Chang、Jian-Cheng Lee、Fung-E. Hong

  DOI：10.1021/om050060j

  日期：2005.11.1

  The preparation and characterization of a novel dicobalt-containing monophosphine ligand, 4a, is presented. Palladium-catalyzed Suzuki-Miyuara reactions employing 4a/Pd(OAc)(2) were pursued. The optimized reaction conditions were found to start with 1 molar equiv of aryllialides, 1.5-fold of phenylbronic acid, 3-fold of KF in 1 mL of THF, and I mol % of 4a/Pd(OAc)2 as catalytic precursor. The P-31 NMR studies reveal moderate reductive capacity of 4a toward Pd(OAc)(2). The unique bonding mode of 4a toward Pd ensures that the ratio of 4a/Pd is equal to 1:1. Two plausible active species, I and [I-OAc](-), were proposed as the catalytically active species in the Suzuki-Miyaura cross-coupling reaction. The validity of this assumption was examined by P-31 NMR spectra and density functional theory (DFT) means. In addition, we have demonstrated theoretically that the dicobalt moiety of 4a acts as an effective auxiliary in stabilizing the Pd(0) center during catalytic reaction.