2-(1-naphthalenylphenyl)pyridine

• 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: 2-(1-naphthalenylphenyl)pyridine
• 英文别名: 2-(2-(naphthalen-1-yl)phenyl)pyridine；2-(2-Naphthalen-1-ylphenyl)pyridine
• 化学式: C₂₁H₁₅N
• 分子量: 281.357
• InChiKey: XWNTWCZSKZAUMG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-(1-naphthalenylphenyl)pyridine 、 9-borabicyclo[3.3.1]nonane dimer 在 palladium diacetate 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 24.0h， 以77%的产率得到2-[2-(9-borabicyclo[3.3.1]-9-nonyl)-1-naphthalenyl]pyridine
  参考文献：
  名称：

  钯催化的邻选择性Ç ？室温下2-苯基吡啶及其衍生物的氢硼化

  摘要：

  硼递送：C  H在硼化邻芳族化合物的位上由处理2-苯基吡啶的，或它的衍生物在钯催化剂的存在下促进，与9-硼双环[3.3.1]壬烷。该反应在室温下进行，并且可以在不使用钯催化剂的情况下在较高温度下进行。在这两种情况下，区域选择性均受硼和氮原子之间路易斯酸碱相互作用的控制。

  DOI：

  10.1002/anie.201210328
• 作为产物：
  描述：

  三正丁基2-吡啶基锌 在 bis(1,5-cyclooctadiene)nickel (0) 、 四(三苯基膦)钯 、 cesium fluoride 、 三环己基膦 作用下， 以 甲苯 为溶剂， 反应 12.0h， 生成 2-(1-naphthalenylphenyl)pyridine
  参考文献：
  名称：

  Nickel-Catalyzed Suzuki–Miyaura Reaction of Aryl Fluorides

  摘要：

  Two protocols for the nickel-catalyzed cross-coupling of aryl fluorides with aryl boronic esters have been developed. The first employs metal fluoride cocatalysts, such as ZrF4 and TiF4, which enable Suzuki-Miyaura reactions of aryl fluorides bearing electron-withdrawing (ketones, esters, and CF3), aryl and alkenyl groups as well as those comprising fused aromatic rings, such as fluoronaphthalenes and fluoroquinolines. The second protocol employs aryl fluorides bearing ortho-directing groups, which facilitate the difficult C-F bond activation process via cyclometalation. N-heterocycles, such as pyridines, quinolines, pyrazoles, and oxazolines, can successfully promote cross-coupling with an array of organoboronic esters. A study into the substituent effects with respect to both coupling components has provided fundamental insights into the mechanism of the nickel-catalyzed cross-coupling of aryl fluorides.

  DOI：

  10.1021/ja207759e

文献信息

• Palladium-Catalyzed<i>ortho</i>-Selective CH Borylation of 2-Phenylpyridine and Its Derivatives at Room Temperature
  作者：Yoichiro Kuninobu、Takashi Iwanaga、Tetsuya Omura、Kazuhiko Takai

  DOI：10.1002/anie.201210328

  日期：2013.4.15

  Boron delivery: CH borylation at the ortho‐position of aromatic compounds is promoted by the treatment of 2‐phenylpyridine, or its derivatives, with 9‐borabicyclo[3.3.1]nonane in the presence of a palladium catalyst. This reaction proceeds at room temperature and can be conducted without the palladium catalyst at higher temperatures. In both cases, the regioselectivity is controlled by Lewis acid–base

  硼递送：C  H在硼化邻芳族化合物的位上由处理2-苯基吡啶的，或它的衍生物在钯催化剂的存在下促进，与9-硼双环[3.3.1]壬烷。该反应在室温下进行，并且可以在不使用钯催化剂的情况下在较高温度下进行。在这两种情况下，区域选择性均受硼和氮原子之间路易斯酸碱相互作用的控制。
• Ruthenium Complex-Catalyzed Direct Ortho Arylation and Alkenylation of 2-Arylpyridines with Organic Halides
  作者：Shuichi Oi、Susumu Fukita、Naoki Hirata、Noboru Watanuki、Sotaro Miyano、Yoshio Inoue

  DOI：10.1021/ol016257z

  日期：2001.8.9

  [GRAPHICS]The ortho position of the aromatic ring of pyridyl group-substituted aromatic compounds is directly arylated or alkenylated with organic halides in the presence of a catalytic amount of a ruthenium(II)-phosphine complex.
• Nickel-Catalyzed Suzuki–Miyaura Reaction of Aryl Fluorides
  作者：Mamoru Tobisu、Tian Xu、Toshiaki Shimasaki、Naoto Chatani

  DOI：10.1021/ja207759e

  日期：2011.12.7

  Two protocols for the nickel-catalyzed cross-coupling of aryl fluorides with aryl boronic esters have been developed. The first employs metal fluoride cocatalysts, such as ZrF4 and TiF4, which enable Suzuki-Miyaura reactions of aryl fluorides bearing electron-withdrawing (ketones, esters, and CF3), aryl and alkenyl groups as well as those comprising fused aromatic rings, such as fluoronaphthalenes and fluoroquinolines. The second protocol employs aryl fluorides bearing ortho-directing groups, which facilitate the difficult C-F bond activation process via cyclometalation. N-heterocycles, such as pyridines, quinolines, pyrazoles, and oxazolines, can successfully promote cross-coupling with an array of organoboronic esters. A study into the substituent effects with respect to both coupling components has provided fundamental insights into the mechanism of the nickel-catalyzed cross-coupling of aryl fluorides.