Pd(2-picolinate)(PPh₃)(OTs) | 228575-92-6

• 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: Pd(2-picolinate)(PPh₃)(OTs)
• 英文别名: Pd(pyca)(PPh₃)(OTs)；Pd(picolinate)(PPh3)(OTs)；4-Methylbenzenesulfonate;palladium(2+);pyridine-2-carboxylate;triphenylphosphane
• CAS: 228575-92-6；228720-39-6
• 化学式: C₃₁H₂₆NO₅PPdS
• 分子量: 662.011
• InChiKey: YKEQHPCWWLBBNM-UHFFFAOYSA-L

计算性质

• 辛醇/水分配系数(LogP)：
  3.79
• 重原子数：
  40
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.03
• 拓扑面积：
  119
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  triphenylphosphine trisulfonate 、 Pd(2-picolinate)(PPh₃)(OTs) 以 水 、 丁酮 为溶剂， 生成
  参考文献：
  名称：

  Biphasic carbonylation of vinyl aromatic compounds using novel water-soluble Pd catalyst: activity, selectivity and mechanistic studies

  摘要：

  The biphasic carbonylation of vinyl aromatic compounds to the isomeric arylpropanoic acids has been studied in detail using a novel water-soluble palladium complex, [Pd(Pyca)(TPPTS)]+TsO-. The effect of various reaction and catalyst parameters such as promoters, solvents, P/Pd ratio, CO partial pressure, temperature and concentration of substrate on the catalytic activity and selectivity has been investigated using styrene as the model substrate. High catalytic activity (TOF = 282 h(-1)) and selectivity to the branched product (similar to91 %) was observed with [Pd(Pyca)(TPPTS)]+TsO- catalyst. P-31 NMR experiments were carried out to study the mechanistic details and to understand the nature of catalytic species formed under the reaction conditions, based on which a plausible catalytic cycle has been proposed. (C) 2002 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s1381-1169(01)00367-3
• 作为产物：
  描述：

  2-吡啶甲酸 、 palladium diacetate 、 对甲苯磺酸 、 三苯基膦 以 氯仿 为溶剂， 以88%的产率得到Pd(2-picolinate)(PPh₃)(OTs)
  参考文献：
  名称：

  使用膦修饰的 Pd(II)-吡啶甲酸酯络合物进行高效的 Mizoroki-Heck 偶联反应

  摘要：

  摘要 高效的 Mizoroki-Heck 偶联是使用一种非常容易合成的半稳定 N-O 配体（吡啶甲酸）的钯 (II) 复合物获得的，具有高达 >10,000 h-1 的高周转频率，仅需 15 分钟，具有 > 99% 达到所需产品。外观简单的钯配合物催化剂的广泛适用性是通过不同功能化的底物建立的。催化剂筛选研究揭示了催化剂性能对不同反应参数和条件的依赖性的复杂细节，并得出了优化的简便方法。图形概要

  DOI：

  10.1080/00397911.2018.1428347
• 作为试剂：
  描述：

  Alpha-甲基苯乙烯 、 4-碘苯甲醚 在 Pd(2-picolinate)(PPh₃)(OTs) 、 sodium acetate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.25h， 以90%的产率得到(E)-4'-methoxy-4-methylstilbene
  参考文献：
  名称：

  使用膦修饰的 Pd(II)-吡啶甲酸酯络合物进行高效的 Mizoroki-Heck 偶联反应

  摘要：

  摘要 高效的 Mizoroki-Heck 偶联是使用一种非常容易合成的半稳定 N-O 配体（吡啶甲酸）的钯 (II) 复合物获得的，具有高达 >10,000 h-1 的高周转频率，仅需 15 分钟，具有 > 99% 达到所需产品。外观简单的钯配合物催化剂的广泛适用性是通过不同功能化的底物建立的。催化剂筛选研究揭示了催化剂性能对不同反应参数和条件的依赖性的复杂细节，并得出了优化的简便方法。图形概要

  DOI：

  10.1080/00397911.2018.1428347

文献信息

• Anchored Pd-complexes in mesoporous supports: Synthesis, characterization and catalysis studies for carbonylation reactions
  作者：Bibhas R. Sarkar、Raghunath V. Chaudhari

  DOI：10.1016/j.cattod.2012.04.047

  日期：2012.12

  Pd(pyca)(PPh3)(OTs) [pyca = 2-picolinate] complex is efficiently anchored inside different mesoporous matrices, such as MCM-41, MCM-48, SBA-15 using a molecular aminopropyl tether moiety employing different synthesis strategies. Thorough characterization of the materials using powder XRD, multinuclear (C-13, Si-29, P-31) CP-MAS NMR, XPS, SEM, N-2-sorption studies etc. confirmed the successful anchoring of the palladium complex to the walls of the support matrices thus establishing the synthesis protocols unambiguously. The catalysts were found to be highly active and selective for the carbonylation of different aryl olefins and alcohols. Consecutive recycling and successful reuse proved the stability and true heterogeneous nature of all the anchored catalysts, which is a substantial advancement over the existing heterogeneous catalysts for carbonylation. (C) 2012 Elsevier B. V. All rights reserved.
• Efficient Mizoroki–Heck coupling reactions using phosphine-modified Pd(II)–picolinate complex
  作者：Sonam Sharma、Bibhas R. Sarkar

  DOI：10.1080/00397911.2018.1428347

  日期：2018.4.18

  ABSTRACT Efficient Mizoroki–Heck couplings were obtained using a very easily synthesizable palladium(II) complex of hemilabile N–O ligand (picolinate), with high turnover frequencies up to >10,000 h−1, in just 15 min, with high selectivity of >99% to the desired products. Wide applicability of the simple-looking palladium complex catalyst was established with differently functionalized substrates.

  摘要 高效的 Mizoroki-Heck 偶联是使用一种非常容易合成的半稳定 N-O 配体（吡啶甲酸）的钯 (II) 复合物获得的，具有高达 >10,000 h-1 的高周转频率，仅需 15 分钟，具有 > 99% 达到所需产品。外观简单的钯配合物催化剂的广泛适用性是通过不同功能化的底物建立的。催化剂筛选研究揭示了催化剂性能对不同反应参数和条件的依赖性的复杂细节，并得出了优化的简便方法。图形概要
• Biphasic carbonylation of vinyl aromatic compounds using novel water-soluble Pd catalyst: activity, selectivity and mechanistic studies
  作者：S Jayasree

  DOI：10.1016/s1381-1169(01)00367-3

  日期：2002.3.25

  The biphasic carbonylation of vinyl aromatic compounds to the isomeric arylpropanoic acids has been studied in detail using a novel water-soluble palladium complex, [Pd(Pyca)(TPPTS)]+TsO-. The effect of various reaction and catalyst parameters such as promoters, solvents, P/Pd ratio, CO partial pressure, temperature and concentration of substrate on the catalytic activity and selectivity has been investigated using styrene as the model substrate. High catalytic activity (TOF = 282 h(-1)) and selectivity to the branched product (similar to91 %) was observed with [Pd(Pyca)(TPPTS)]+TsO- catalyst. P-31 NMR experiments were carried out to study the mechanistic details and to understand the nature of catalytic species formed under the reaction conditions, based on which a plausible catalytic cycle has been proposed. (C) 2002 Elsevier Science B.V. All rights reserved.