3,6-dibromo-2-methyl-2,1-borazaronaphthalene | 1616635-15-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 3,6-dibromo-2-methyl-2,1-borazaronaphthalene
• CAS: 1616635-15-4
• 化学式: C₉H₈BBr₂N
• 分子量: 300.788
• InChiKey: BZNMXDPIZLTUFF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.77
• 重原子数：
  13.0
• 可旋转键数：
  0.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  12.03
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  3,6-dibromo-2-methyl-2,1-borazaronaphthalene 、 (3-甲氧基苯基)三氟硼酸钾 在 chloro[(tri-tert-butylphosphine)-2-(2-aminobiphenyl)]palladium (II) 、 caesium carbonate 作用下， 以 水 为溶剂， 反应 18.0h， 以97%的产率得到3,6-bis(3-Methoxyphenyl)-2-methyl-2,1-borazaronaphthalene
  参考文献：
  名称：

  Accessing Molecularly Complex Azaborines: Palladium-Catalyzed Suzuki–Miyaura Cross-Couplings of Brominated 2,1-Borazaronaphthalenes and Potassium Organotrifluoroborates

  摘要：

  Despite their potential applications in both medicinal chemistry and materials science, there have been limited reports on the functionalization of 2,1-borazaronaphthalenes since their discovery in 1959. To access new chemical space and build molecular complexity, the Suzuki-Miyaura cross-coupling of brominated 2,1-borazaronaphthalenes been investigated. The palladium-catalyzed cross-coupling proceeds with an array of potassium (hetero)aryltrifluoroborates in high yield with low catalyst loadings under mild reaction conditions. By the use of a high-yielding bromination of various 2,1-borazaronaphthalenes to generate electrophilic azaborine species, a library of 3-(hetero)aryl and 3,6-diaryl-2,1-borazaronaphthalenes has been synthesized.

  DOI：

  10.1021/jo5011894
• 作为产物：
  描述：

  2-methyl-2,1-borazaronaphthalene 在 溴 作用下， 以 二氯甲烷 为溶剂， 以92%的产率得到3,6-dibromo-2-methyl-2,1-borazaronaphthalene
  参考文献：
  名称：

  Accessing Molecularly Complex Azaborines: Palladium-Catalyzed Suzuki–Miyaura Cross-Couplings of Brominated 2,1-Borazaronaphthalenes and Potassium Organotrifluoroborates

  摘要：

  Despite their potential applications in both medicinal chemistry and materials science, there have been limited reports on the functionalization of 2,1-borazaronaphthalenes since their discovery in 1959. To access new chemical space and build molecular complexity, the Suzuki-Miyaura cross-coupling of brominated 2,1-borazaronaphthalenes been investigated. The palladium-catalyzed cross-coupling proceeds with an array of potassium (hetero)aryltrifluoroborates in high yield with low catalyst loadings under mild reaction conditions. By the use of a high-yielding bromination of various 2,1-borazaronaphthalenes to generate electrophilic azaborine species, a library of 3-(hetero)aryl and 3,6-diaryl-2,1-borazaronaphthalenes has been synthesized.

  DOI：

  10.1021/jo5011894

文献信息

• Suzuki–Miyaura Cross-Coupling of Brominated 2,1-Borazaronaphthalenes with Potassium Alkenyltrifluoroborates
  作者：Gary A. Molander、Steven R. Wisniewski、Elham Etemadi-Davan

  DOI：10.1021/jo502260x

  日期：2014.11.21

  Conditions have been developed for the palladium-catalyzed cross-coupling of 3-bromo-2,1-borazaronaphthalenes with potassium alkenyltrifluoroborates. Twenty-seven alkenyl-substituted azaborines have been synthesized through this method, providing access to a family of 2,1-borazaronaphthalenes with alkenyl substitution at the C3 position.