9-(3-bromo-4-iodophenyl)-9H-carbazole

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 9-(3-bromo-4-iodophenyl)-9H-carbazole
• 英文别名: 9-(3-Bromo-4-iodophenyl)-9H-carbazole；9-(3-bromo-4-iodophenyl)carbazole
• 化学式: C₁₈H₁₁BrIN
• 分子量: 448.101
• InChiKey: RWBPGBSMBCWDBT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  4.9
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  9-(3-bromo-4-iodophenyl)-9H-carbazole 在 copper(l) iodide 、 四(三苯基膦)钯 、 正丁基锂 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 正己烷 、 水 为溶剂， 反应 28.0h， 生成 9-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-4-((triisopropylsilyl)ethynyl)phenyl)-9H-carbazole
  参考文献：
  名称：

  具有双齿二乙炔配体的发光铂 (II) 配合物：结构、光物理特性和应用研究

  摘要：

  已经制备了一系列由三联苯二乙炔以及二亚胺或双-N-杂环卡宾 (NHC) 配体负载的铂 (II) 配合物。二乙炔配体采用顺式配位模式，具有非平面的三联苯部分。此外，还研究了这些铂 (II) 配合物的电化学、光物理和光化学性质。

  DOI：

  10.1002/asia.202100756
• 作为产物：
  描述：

  咔唑 、 2-溴-4-氟-1-碘苯 在 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以85%的产率得到9-(3-bromo-4-iodophenyl)-9H-carbazole
  参考文献：
  名称：

  Site-Selective N-Arylation of Carbazoles with Halogenated Fluorobenzenes

  摘要：

  A method for the highly site-selective C-N bond-formation reaction of halogenated fluorobenzenes with carbazoles is described. The selectivity of iodine and fluorine atoms on the aromatic ring of fluorinated iodobenzenes was initially determined with a copper-N,N-diisopropylethylamine catalytic system. By changing the position of the iodine atom on the aromatic ring from the 3- or 4-position to the 2-position, the preferred coupling site was switched from the iodine atom to the fluorine atom. Steric hindrance of the fluorinated iodobenzenes is responsible for the selectivity switch. After elucidating the reaction mechanisms of these reaction processes, a metal-free method for the highly site-selective C-N bond-formation reaction of halogenated fluorobenzenes with carbazoles was revealed through C-F bond activation. The metal-free system is able to handle a range of halogenated groups. Thus, a broad range of chlorinated, brominated, and iodinated N-arylated carbazoles were generated, which are widely useful in organic chemistry.

  DOI：

  10.1055/s-0035-1560386

文献信息

• MATERIALIEN FÜR ORGANISCHE ELEKTROLUMINESZENZVORRICHTUNGEN
  申请人：Merck Patent GmbH

  公开号：EP3335254B1

  公开（公告）日：2020-04-08
• [DE] MATERIALIEN FÜR ORGANISCHE ELEKTROLUMINESZENZVORRICHTUNGEN<br/>[EN] MATERIALS FOR ORGANIC ELECTROLUMINESCENT DEVICES<br/>[FR] MATÉRIAUX POUR DISPOSITIFS ÉLECTROLUMINESCENTS ORGANIQUES
  申请人：MERCK PATENT GMBH

  公开号：WO2017025164A1

  公开（公告）日：2017-02-16

  Die vorliegende Erfindung betrifft Verbindungen, die sich für die Verwendung in elektronischen Vorrichtungen eignen, sowie elektronische Vorrichtungen, insbesondere organischen Elektrolumineszenzvorrichtungen, enthaltend diese Verbindungen.
• Luminescent Platinum(II) Complexes with Bidentate Diacetylide Ligands: Structures, Photophysical Properties and Application Studies
  作者：Zaoli Luo、Yungen Liu、Ka‐Chung Tong、Xiao‐Yong Chang、Wai‐Pong To、Chi‐Ming Che

  DOI：10.1002/asia.202100756

  日期：2021.10.4

  A series of platinum(II) complexes supported by terphenyl diacetylide as well as diimine or bis-N-heterocyclic carbene (NHC) ligands have been prepared. The diacetylide ligands adopt a cis coordination mode featuring non-planar terphenyl moieties. Furthermore, the electrochemical, photophysical and photochemical properties of these platinum(II) complexes have been investigated.

  已经制备了一系列由三联苯二乙炔以及二亚胺或双-N-杂环卡宾 (NHC) 配体负载的铂 (II) 配合物。二乙炔配体采用顺式配位模式，具有非平面的三联苯部分。此外，还研究了这些铂 (II) 配合物的电化学、光物理和光化学性质。
• Site-Selective N-Arylation of Carbazoles with Halogenated Fluorobenzenes
  作者：Ning Liu、Bin Dai、Lei Wang、Enhui Ji

  DOI：10.1055/s-0035-1560386

  日期：——

  A method for the highly site-selective C-N bond-formation reaction of halogenated fluorobenzenes with carbazoles is described. The selectivity of iodine and fluorine atoms on the aromatic ring of fluorinated iodobenzenes was initially determined with a copper-N,N-diisopropylethylamine catalytic system. By changing the position of the iodine atom on the aromatic ring from the 3- or 4-position to the 2-position, the preferred coupling site was switched from the iodine atom to the fluorine atom. Steric hindrance of the fluorinated iodobenzenes is responsible for the selectivity switch. After elucidating the reaction mechanisms of these reaction processes, a metal-free method for the highly site-selective C-N bond-formation reaction of halogenated fluorobenzenes with carbazoles was revealed through C-F bond activation. The metal-free system is able to handle a range of halogenated groups. Thus, a broad range of chlorinated, brominated, and iodinated N-arylated carbazoles were generated, which are widely useful in organic chemistry.