6'-bromo-5-chloro-2,2'-bipyridine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 6'-bromo-5-chloro-2,2'-bipyridine
• 英文别名: 2-Bromo-6-(5-chloropyridin-2-yl)pyridine
• 化学式: C₁₀H₆BrClN₂
• 分子量: 269.528
• InChiKey: AMQDZQCRSJFPCT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  25.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2,6-二溴吡啶 、 2-溴-5-氯吡啶 在 异丙基氯化镁 、 三丁基氯化锡 、 四(三苯基膦)钯 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 28.5h， 生成 6'-bromo-5-chloro-2,2'-bipyridine
  参考文献：
  名称：

  Enantioconvergent Cu-Catalyzed Intramolecular C–C Coupling at Boron-Bound C(sp³) Atoms of α-Aminoalkylboronates Using a C₁-Symmetrical 2,2′-Bipyridyl Ligand Attached to a Helically Chiral Macromolecular Scaffold

  摘要：

  Enantioconvergent intramolecular coupling of alpha-(2-bromobenzoylamino)benzylboronic esters was achieved using a copper catalyst having helically chiral macromolecular bipyridyl ligand, PQXbpy. Racemic alpha-(2-bromobenzoylamino)benzylboronic esters were converted into (R)-configured 3-arylisoindolinones with high enantiopurity using right-handed helical PQXbpy as a chiral ligand in a toluene/CHCI3 mixed solvent. When enantiopure (R)- and (S)-configured boronates were separately reacted under the same reaction conditions, both afforded (R)-configured products through formal stereoinvertive and stereoretentive processes, respectively. From these results, a mechanism involving deracemization of organocopper intermediates in the presence of PQXbpy is assumed. PQXbpy switched its helical sense to left-handed when a toluene/1,1,2-trichloroethane mixed solvent was used, resulting in the formation of the corresponding (S)-products from the racemic starting material.

  DOI：

  10.1021/jacs.0c09080

文献信息

• Enantioconvergent Cu-Catalyzed Intramolecular C–C Coupling at Boron-Bound C(sp³) Atoms of α-Aminoalkylboronates Using a <i>C</i>₁-Symmetrical 2,2′-Bipyridyl Ligand Attached to a Helically Chiral Macromolecular Scaffold
  作者：Yukako Yoshinaga、Takeshi Yamamoto、Michinori Suginome

  DOI：10.1021/jacs.0c09080

  日期：2020.10.28

  Enantioconvergent intramolecular coupling of alpha-(2-bromobenzoylamino)benzylboronic esters was achieved using a copper catalyst having helically chiral macromolecular bipyridyl ligand, PQXbpy. Racemic alpha-(2-bromobenzoylamino)benzylboronic esters were converted into (R)-configured 3-arylisoindolinones with high enantiopurity using right-handed helical PQXbpy as a chiral ligand in a toluene/CHCI3 mixed solvent. When enantiopure (R)- and (S)-configured boronates were separately reacted under the same reaction conditions, both afforded (R)-configured products through formal stereoinvertive and stereoretentive processes, respectively. From these results, a mechanism involving deracemization of organocopper intermediates in the presence of PQXbpy is assumed. PQXbpy switched its helical sense to left-handed when a toluene/1,1,2-trichloroethane mixed solvent was used, resulting in the formation of the corresponding (S)-products from the racemic starting material.