(2-iodophenoxy)methyl-trimethylstannane | 162462-75-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (2-iodophenoxy)methyl-trimethylstannane
• CAS: 162462-75-1
• 化学式: C₁₀H₁₅IOSn
• 分子量: 396.843
• InChiKey: FMFGPPUMSBUWSK-UHFFFAOYSA-N

物化性质

• 沸点：
  330.5±52.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.55
• 重原子数：
  13.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  9.23
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  四(三苯基膦)钯 、 (2-iodophenoxy)methyl-trimethylstannane 以 甲苯 为溶剂， 以75%的产率得到bis(triphenylphosphine)(methyleneoxy-1,2-phenylene)palladium
  参考文献：
  名称：

  Cardenas, Diego J.; Mateo, Cristina; Echavarren, Antonio M., Angewandte Chemie, 1994, vol. 106, # 23/24, p. 2529 - 2531

  摘要：

  DOI：

文献信息

• Mechanistic Significance of the Si–O–Pd Bond in the Palladium-Catalyzed Cross-Coupling Reactions of Alkenylsilanolates
  作者：Steven A. Tymonko、Russell C. Smith、Andrea Ambrosi、Scott E. Denmark

  DOI：10.1021/jacs.5b02515

  日期：2015.5.20

  Through the combination of reaction kinetics (both catalytic and stoichiometric) and solid-state characterization of arylpalladium(II) alkenylsilanolate complexes, the intermediacy of covalent adducts containing Si-O-Pd linkages in the cross-coupling reactions of organosilanolates has been unambiguously established. Two mechanistically distinct pathways have been demonstrated: (1), transmetalation via a neutral 8-Si-4 intermediate that dominates in the cross-coupling of potassium allenylsilanolates, and (2) transmetalation via an anionic 10-Si-5 intermediate that dominates in the cross-coupling of cesium alkenylsilanolates. Arylpalladium(II) alkenylsilanolate complexes bearing various phosphine ligands (both bidentate and monodentate) have been isolated, frilly characterized, and evaluated for their kinetic, competence under thermal (stoichiometric) and anionic (catalytic) conditions. Comparison of the rates for thermal and anionic activation demonstrates that intermediates containing the Si-O-Pd linkage are involved in the cross-coupling process.