2-(2,4-dichlorophenoxy)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane | 2095797-31-0

• 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-(2,4-dichlorophenoxy)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• 英文别名: 1,3,2-Dioxaborolane, 2-(2,4-dichlorophenoxy)-4,4,5,5-tetramethyl-
• CAS: 2095797-31-0
• 化学式: C₁₂H₁₅BCl₂O₃
• 分子量: 288.966
• InChiKey: QVLGRGCPTRYRDE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.96
• 重原子数：
  18.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  27.69
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2-(2,4-dichlorophenoxy)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 、 联硼酸频那醇酯 在 (1,5-cyclooctadiene)(methoxy)iridium(I) dimer 、 4,4'-二叔丁基-2,2'-二吡啶 作用下， 以 环己烷 为溶剂， 以49 %的产率得到
  参考文献：
  名称：

  Ir-Catalyzed ortho-Borylation of Phenols Directed by Substrate–Ligand Electrostatic Interactions: A Combined Experimental/in Silico Strategy for Optimizing Weak Interactions

  摘要：

  A strategy for affecting ortho-versus meta/para selectivity in Ir-catalyzed C-H borylations (CHBs) of phenols is described. From selectivity observations with ArylOBpin (pin-7 pinacolate), it is hypothesized that an electrostatic interaction between the partial negatively,charged OBpin group and the partial positively charged bipyridine ligand of the catalyst favors ortho selectivity. Experimental and computational studies designed to test this hypothesis support it. From further computational work a second generation, in silico designed catalyst emerged; where replacing Bpin with Beg (eg, = ethylene glycolate) was predicted to significantly improve ortho selectivity. Experinientally, reactions employing B(2)eg(2) gave ortho selectivities > 99%. Adding triethylamine significantly improved conversions. This ligand-substrate electrostatic interaction provides a unique control element for selective C-H functionalization.

  DOI：

  10.1021/jacs.7b02232
• 作为产物：
  描述：

  2,4-二氯酚 、 频那醇硼烷 以 neat (no solvent) 为溶剂， 生成 2-(2,4-dichlorophenoxy)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
  参考文献：
  名称：

  Ir-Catalyzed ortho-Borylation of Phenols Directed by Substrate–Ligand Electrostatic Interactions: A Combined Experimental/in Silico Strategy for Optimizing Weak Interactions

  摘要：

  A strategy for affecting ortho-versus meta/para selectivity in Ir-catalyzed C-H borylations (CHBs) of phenols is described. From selectivity observations with ArylOBpin (pin-7 pinacolate), it is hypothesized that an electrostatic interaction between the partial negatively,charged OBpin group and the partial positively charged bipyridine ligand of the catalyst favors ortho selectivity. Experimental and computational studies designed to test this hypothesis support it. From further computational work a second generation, in silico designed catalyst emerged; where replacing Bpin with Beg (eg, = ethylene glycolate) was predicted to significantly improve ortho selectivity. Experinientally, reactions employing B(2)eg(2) gave ortho selectivities > 99%. Adding triethylamine significantly improved conversions. This ligand-substrate electrostatic interaction provides a unique control element for selective C-H functionalization.

  DOI：

  10.1021/jacs.7b02232