2'-Methoxy[1,1'-biphenyl]-3-carbonitrile | 154848-37-0

• 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'-Methoxy[1,1'-biphenyl]-3-carbonitrile
• 英文别名: 3-(2-methoxyphenyl)benzonitrile
• CAS: 154848-37-0
• 化学式: C₁₄H₁₁NO
• 分子量: 209.247
• InChiKey: ZLJZSLGPFPECRA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  33
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  间溴苯甲腈 、 2-甲氧基苯基硼酸 在 dichloro[1,1'-bis(di-t-butylphosphino)ferrocene]palladium(II) 、 potassium carbonate 作用下， 以 水 、 乙腈 为溶剂， 生成 2'-Methoxy[1,1'-biphenyl]-3-carbonitrile
  参考文献：
  名称：

  A mild robust generic protocol for the Suzuki reaction using an air stable catalyst

  摘要：

  A mild but robust procedure has been developed as a first pass generic protocol for the Suzuki-Miyaura reaction. The protocol employs an air stable palladium pre-catalyst at low loading (<= 1 mol %) in aqueous solvent mixtures at moderate temperature using potassium carbonate as base. Under these mild conditions, most aryl bromides will react with sterically and electronically demanding aryl boronic acids to give complete conversion to the product biphenyls in less than 1 h. Aryl chlorides are also fully converted in most cases either under identical conditions in 8-24 h, or in 2 h at elevated temperature. A further advantage of these mild conditions of moderate temperature, weak base and benign solvent is that sensitive functional groups and structural motifs are well tolerated. In addition, the lipophilic biphenyl products are readily isolated after a simple work-up procedure. These generic conditions are ideal for proof of transformation, and as the starting point for development and optimization of a specific process. The discovery and fine-tuning of this generic protocol will be presented, supported extensively by examples to illustrate its scope and utility. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.05.030

文献信息

• A mild robust generic protocol for the Suzuki reaction using an air stable catalyst
  作者：Jonathan D. Moseley、Paul M. Murray、Edward R. Turp、Simon N.G. Tyler、Ross T. Burn

  DOI：10.1016/j.tet.2012.05.030

  日期：2012.7

  A mild but robust procedure has been developed as a first pass generic protocol for the Suzuki-Miyaura reaction. The protocol employs an air stable palladium pre-catalyst at low loading (<= 1 mol %) in aqueous solvent mixtures at moderate temperature using potassium carbonate as base. Under these mild conditions, most aryl bromides will react with sterically and electronically demanding aryl boronic acids to give complete conversion to the product biphenyls in less than 1 h. Aryl chlorides are also fully converted in most cases either under identical conditions in 8-24 h, or in 2 h at elevated temperature. A further advantage of these mild conditions of moderate temperature, weak base and benign solvent is that sensitive functional groups and structural motifs are well tolerated. In addition, the lipophilic biphenyl products are readily isolated after a simple work-up procedure. These generic conditions are ideal for proof of transformation, and as the starting point for development and optimization of a specific process. The discovery and fine-tuning of this generic protocol will be presented, supported extensively by examples to illustrate its scope and utility. (C) 2012 Elsevier Ltd. All rights reserved.