3-quinolinylzinc bromide | 1207760-36-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 3-quinolinylzinc bromide
• 英文别名: 3-quinolylzinc bromide
• CAS: 1207760-36-8
• 化学式: C₉H₆BrNZn
• 分子量: 273.447
• InChiKey: SJLSNCWDFTYBAH-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  2.25
• 重原子数：
  12.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  12.89
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  3-quinolinylzinc bromide 在 copper(I) chloride bis(lithium chloride) complex 、 3,3’-di-tert-butyl oxaziridine 作用下， 以 四氢呋喃 为溶剂， 反应 0.67h， 以42%的产率得到3-氨基喹啉
  参考文献：
  名称：

  Non-Deprotonative Primary and Secondary Amination of (Hetero)Arylmetals

  摘要：

  Herein we disclose a novel method for the facile transfer of primary (-NH2) and secondary amino groups (-NHR) to heteroaryl- as well as arylcuprates at low temperature without the need for precious metal catalysts, ligands, excess reagents, protecting and/or directing groups. This one-pot transformation allows unprecedented functional group tolerance and it is well suited for the amination of electron-rich, electron-deficient as well as structurally complex (hetero)arylmetals. In some of the cases, only catalytic amounts of a copper(I) salt is required.

  DOI：

  10.1021/jacs.6b12712

文献信息

• Cobalt−Xantphos-Catalyzed, LiCl-Mediated Preparation of Arylzinc Reagents from Aryl Iodides, Bromides, and Chlorides
  作者：Meng-Yi Jin、Naohiko Yoshikai

  DOI：10.1021/jo102417x

  日期：2011.4.1

  A cobalt−Xantphos-catalyzed, LiCl-mediated system has been developed for the direct and expedient preparation of arylzinc reagents in THF from the corresponding aryl iodides, bromides, and chlorides. Owing to the use of THF as a versatile solvent, the thus-formed arylzinc reagents displayed a high degree of compatibility with a variety of conventional as well as newly emerging metal-catalyzed cross-coupling

  已经开发了钴-黄药催化的，LiCl介导的系统，用于从相应的芳基碘化物，溴化物和氯化物直接且方便地制备THF中的芳基锌试剂。由于使用THF作为通用溶剂，因此形成的芳基锌试剂显示出与各种常规以及新兴的金属催化的交叉偶联反应的高度相容性。
• 2-Pyridyl and 3-pyridylzinc bromides: direct preparation and coupling reaction
  作者：Seung-Hoi Kim、Reuben D. Rieke

  DOI：10.1016/j.tet.2010.02.061

  日期：2010.4

  A facile synthetic approach to the direct preparation of 2-pyridyl and 3-pyridylzinc bromides has been demonstrated using Rieke zinc with 2-bromopyridine and 3-bromopyridine, respectively. A variety of different electrophiles have been coupled with the resulting organozinc reagents to give the corresponding cross-coupling products in moderate to good yields.

  已证明使用Rieke锌分别与2-溴吡啶和3-溴吡啶直接合成2-吡啶基和3-吡啶基锌溴化物的简便合成方法。各种不同的亲电试剂已与所得的有机锌试剂偶联，以中等至良好的产率得到相应的交叉偶联产物。
• 5-Substituted-2-furaldehydes: A Synthetic Protocol Utilizing an Organozinc Route
  作者：Seung-Hoi Kim、Reuben D. Rieke

  DOI：10.1021/jo301836x

  日期：2013.3.1

  5-bromo-2-furaldehyde or utilization of a new organozinc reagent, 5-(1,3-dioxolan-2-yl)-2-furanylzinc bromide, which was easily prepared by the direct insertion of highly active zinc to 2-(5-bromofuran-2-yl-1,3-dioxolane. Of special note is the uniqueness of using a new organozinc reagent, representing a first example of the direct synthesis of the corresponding organozinc halide. The subsequent coupling reactions

  已经揭示了用于制备广泛的5-取代的2-呋喃醛的简便的合成途径。它们是通过钯催化的各种芳基和杂芳基卤化锌与5-溴-2-呋喃甲醛的钯催化交叉偶联反应或利用新的有机锌试剂5-（1,3-二氧杂戊环-2-基）-2来完成的。 -呋喃基溴化锌，可通过将高活性锌直接插入2-（5-溴呋喃-2-基-1,3-二氧戊环）轻松制备。特别值得注意的是，使用新型有机锌试剂的独特性直接合成相应的有机锌卤化物的例子，随后在各种类型反应条件下的偶联反应导致形成了一些不同的呋喃衍生物。
• A convenient synthesis of 5-aryl- and 5-heteroaryl-2-furaldehydes by the cross-coupling reaction of organozincs
  作者：Seung-Hoi Kim、Reuben D. Rieke

  DOI：10.1016/j.tetlet.2010.03.035

  日期：2010.5

  An efficient synthetic route for the preparation of 5-heteroaryl- and 5-aryl-2-furaldehydes has been developed. It has been accomplished by the palladium(0)-catalyzed cross-coupling reaction of heteroarylzinc and arylzinc reagents with 5-bromo-2-furaldehyde under very mild conditions. (C) 2010 Elsevier Ltd. All rights reserved.