4-(1,3,2-二氧杂环戊硼烷-2-基)苯酚 | 108305-41-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 中文名称: 4-(1,3,2-二氧杂环戊硼烷-2-基)苯酚
• 英文名称: 2-(4-hydroxyphenyl)-1,3,2-dioxaborolane
• 英文别名: 4-(1,3,2-Dioxaborolan-2-yl)phenol
• CAS: 108305-41-5
• 化学式: C₈H₉BO₃
• 分子量: 163.969
• InChiKey: IDSYAEWBNQFQCE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.13
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-羟基苯硼酸 、 乙二醇 以 四氢呋喃 为溶剂， 以79 %的产率得到4-(1,3,2-二氧杂环戊硼烷-2-基)苯酚
  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

文献信息

• Ir-Catalyzed ortho-Borylation of Phenols Directed by Substrate–Ligand Electrostatic Interactions: A Combined Experimental/in Silico Strategy for Optimizing Weak Interactions
  作者：Buddhadeb Chattopadhyay、Jonathan E. Dannatt、Ivonne L. Andujar-De Sanctis、Kristin A. Gore、Robert E. Maleczka、Daniel A. Singleton、Milton R. Smith

  DOI：10.1021/jacs.7b02232

  日期：2017.6.14

  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.