2-(2-(diphenylphosphino)phenyl)-1-methyl-1H-benzoimidazole | 1357398-59-4

• 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-(2-(diphenylphosphino)phenyl)-1-methyl-1H-benzoimidazole
• 英文别名: 1-methyl-2-(2-(diphenylphosphino)phenyl)-1H-benzoimidazole；1-Methyl-2-(2-diphenylphosphinophenyl)-1h-benzoimidazole；[2-(1-methylbenzimidazol-2-yl)phenyl]-diphenylphosphane
• CAS: 1357398-59-4
• 化学式: C₂₆H₂₁N₂P
• 分子量: 392.44
• InChiKey: BVVIYNVQLLTULW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  17.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2-(2-溴苯基)苯并咪唑 在 正丁基锂 、 sodium hydride 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 反应 10.0h， 生成 2-(2-(diphenylphosphino)phenyl)-1-methyl-1H-benzoimidazole
  参考文献：
  名称：

  有效的钯-苯并咪唑基膦配合物用于甲磺酸烷基酯的Suzuki-Miyaura偶联：简便的配体合成和金属配合物表征。

  摘要：

  已经开发出一种新型的易于获得的半不稳定的苯并咪唑基膦配体。配体骨架由可商购的和廉价的邻苯二胺和2-溴苯甲酸制备。在催化剂负载量低至0.5mol％钯的情况下，仍观察到对甲磺酸甲磺酸酯的Suzuki-Miyaura偶联的优异催化活性。通常，这代表了迄今为止该反应所达到的最低催化剂负载量。X射线晶体学表明，新的配体L2以Kappa（2）-P，N的方式与Pd配合。

  DOI：

  10.1039/c2cc15972d

文献信息

• An efficient palladium–benzimidazolyl phosphine complex for the Suzuki–Miyaura coupling of aryl mesylates: facile ligand synthesis and metal complex characterization
  作者：Kin Ho Chung、Chau Ming So、Shun Man Wong、Chi Him Luk、Zhongyuan Zhou、Chak Po Lau、Fuk Yee Kwong

  DOI：10.1039/c2cc15972d

  日期：——

  A new class of easily accessible hemilabile benzimidazolyl phosphine ligands has been developed. The ligand skeleton is prepared from commercially available and inexpensive o-phenylenediamine and 2-bromobenzoic acid. With catalyst loading down to 0.5 mol% palladium, excellent catalytic activity towards the Suzuki-Miyaura coupling of aryl mesylates is still observed. This represents the lowest catalyst

  已经开发出一种新型的易于获得的半不稳定的苯并咪唑基膦配体。配体骨架由可商购的和廉价的邻苯二胺和2-溴苯甲酸制备。在催化剂负载量低至0.5mol％钯的情况下，仍观察到对甲磺酸甲磺酸酯的Suzuki-Miyaura偶联的优异催化活性。通常，这代表了迄今为止该反应所达到的最低催化剂负载量。X射线晶体学表明，新的配体L2以Kappa（2）-P，N的方式与Pd配合。
• Buchwald-Hartwig Amination of Aryl Chlorides Catalyzed by Easily Accessible Benzimidazolyl Phosphine-Pd Complexes
  作者：Chau So、Fuk Kwong、Kin Chung、Shun Wong、Chi Luk、Zhongyuan Zhou、Chak Lau

  DOI：10.1055/s-0031-1290666

  日期：2012.5

  This study describes the efficacy of benzimidazolyl phosphine ligands, which are easily synthesized from inexpensive and commercially available o-phenylenediamine, 2-bormobenzoic acid, and chlorophosphines, in the Buchwald-Hartwig amination of aryl chlorides. Primary and secondary aromatic/aliphatic amines are effective substrates in this catalytic system. Functional groups such as keto and esters are also compatible. The catalyst loading can be reduced to 0.1 mol% Pd.

  本研究描述了从廉价且市售的邻苯二胺、2-溴苯甲酸和氯膦化合物容易合成的苯并咪唭基膦配体在Buchwald-Hartwig芳基氯化物胺化反应中的效能。在该催化体系中，伯和仲芳香/脂肪胺是有效的底物。酮和酯等功能团也能兼容。催化剂负载量可降至0.1 mol% Pd。
• P,N-Type benzimidazolyl phosphine ligands for the palladium-catalyzed Suzuki coupling of potassium aryltrifluoroborates and aryl chlorides
  作者：Shun Man Wong、Chau Ming So、Kin Ho Chung、Chi Him Luk、Chak Po Lau、Fuk Yee Kwong

  DOI：10.1016/j.tetlet.2012.05.017

  日期：2012.7

  describes the efficacy of P,N-type benzimidazolyl phosphine ligands, which can be easily synthesized from commercially available and inexpensive starting materials. The application of this ligand array in palladium-catalyzed Suzuki–Miyaura coupling reaction of aryl chlorides with potassium aryltrifluoroborates is described. The air stable benzimidazolyl phosphines in combination with a palladium metal precursor

  这项研究描述了P，N型苯并咪唑基膦配体的功效，该配体可以很容易地从市售和廉价的原料中合成。描述了这种配体阵列在钯催化的芳基氯与芳基三氟硼酸钾的Suzuki-Miyaura偶联反应中的应用。空气稳定的苯并咪唑基膦与钯金属前体的结合为未活化的芳基氯的Suzuki-Miyaura偶联提供了高效的催化剂，催化剂负载量仅为0.05 mol％。
• LIGAND EXCHANGE THERMOCHROMIC SYSTEMS AND HIGH E LIGANDS FOR SAME
  申请人：Byker J. Harlan

  公开号：US20080105851A1

  公开（公告）日：2008-05-08

  Ligand exchange of thermochromic, LETC, systems exhibiting a reversible change in absorbance of electromagnetic radiation as the temperature of the system is reversibly changed are described. The described LETC systems include one or more than one transition metal ion, which experiences thermally induced changes in the nature of the complexation or coordination around the transition metal ion(s) and, thereby, the system changes its ability to absorb electromagnetic radiation as the temperature changes. In accordance with certain aspects of the present invention, a thermochromic system is disclosed comprising a transition metal ion and a ligand wherein the ligand comprises a nitrogen-containing five or six membered heterocyclic compound that coordinates through the nitrogen atom to the transition metal ion in a HεMLC formed between the transition metal ion and the ligand. In accordance with other aspects of the present invention, thermochromic systems are disclosed comprising a transition metal ion with particularly useful ligands, such as phosphine compounds, tridentate ligands that coordinate through three nitrogen atoms, bidentate ligands, or ortho hindered pyridine monodentate ligands.

  本文描述了具有热致变色性质的配体交换（LETC）系统，当系统的温度可逆变化时，电磁辐射吸收率也可逆变化。所述的LETC系统包括一个或多个过渡金属离子，其经历热诱导的配位或配位环境的变化，从而使系统随着温度变化而改变吸收电磁辐射的能力。根据本发明的某些方面，公开了包括过渡金属离子和配体的热致变色系统，其中配体包括通过氮原子与过渡金属离子形成的HεMLC（配体与过渡金属离子之间的配位键）的含氮五元或六元杂环化合物。根据本发明的其他方面，公开了包括具有特别有用的配体的过渡金属离子的热致变色系统，例如膦化合物、通过三个氮原子配位的三齿配体、双齿配体或邻位受阻的吡啶单齿配体。
• LIGAND EXCHANGE THERMOCHROMIC SYSTEMS CONTAINING EXCHANGE METALS
  申请人：Byker J. Harlan

  公开号：US20080106781A1

  公开（公告）日：2008-05-08

  Ligand exchange of thermochromic, LETC, systems exhibiting a reversible change in absorbance of electromagnetic radiation as the temperature of the system is reversibly changed are described. The described LETC systems include one or more than one transition metal ion, which experiences thermally induced changes in the nature of the complexation or coordination around the transition metal ion(s) and, thereby, the system changes its ability to absorb electromagnetic radiation as the temperature changes. In accordance with one aspect of the present invention, a thermochromic system is disclosed comprising a first metal ion and a second metal ion and at least one ligand that complexes with the first metal ion to form a LεMLC and complexes with the second metal ion to form a HεMLC wherein an increase in temperature of the system results in a reversible net increase in its ability to absorb light energy in the 400 nm to 1400 nm range due to the ligand transferring from the first metal ion to the second metal ion.

  本文介绍了一种具有热致变色特性的配体交换系统，当系统的温度可逆变化时，其吸收电磁辐射的能力也可逆变化。所述的LETC系统包括一个或多个过渡金属离子，其在过渡金属离子周围的络合或配位发生热诱导变化，从而使系统随着温度变化而改变吸收电磁辐射的能力。根据本发明的一个方面，公开了一种热致变色系统，包括第一金属离子和第二金属离子以及至少一个配体，该配体与第一金属离子形成LεMLC配合物，并与第二金属离子形成HεMLC配合物，系统温度的升高导致可逆的净吸收光能力增加，范围为400纳米至1400纳米，这是由于配体从第一金属离子转移到第二金属离子造成的。