1-methyl-2-[2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-1H-imidazole | 1349171-35-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-methyl-2-[2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-1H-imidazole
• 英文别名: 1-Methyl-2-[2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]imidazole
• CAS: 1349171-35-2
• 化学式: C₁₆H₂₁BN₂O₂
• 分子量: 284.166
• InChiKey: RRFXEPIATRKDEV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.39
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  36.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1-甲基-2-苯基-1H-咪唑 、 联硼酸频那醇酯 在 [Rh(OH)(cod)]2 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以100%的产率得到1-methyl-2-[2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-1H-imidazole
  参考文献：
  名称：

  Rh-Catalyzed Ortho-Selective C–H Borylation of N-Functionalized Arenes with Silica-Supported Bridgehead Monophosphine Ligands

  摘要：

  Supported phosphine-Rh systems, prepared in situ from silica-supported bridgehead monophosphines and [Rh(OH)(cod)]2, have enabled ortho-selective C-H borylation for a range of arenes containing nitrogen-based directing groups. The regioselectivity was excellent with various N-directing groups, including saturated and unsaturated N-heterocycles, tert-aminoalkyl groups, and iminetype C-N double bonds. The reaction showed significant tolerance toward steric repulsion around the reacting C-H bond. This Rh catalysis complements the Jr-catalyzed orthoborylation, which is effective for arenes with oxygen-based directing groups.

  DOI：

  10.1021/ja208364a