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Efficient Preparation of Biaryl Compounds and Its Application

联芳基化合物的高效制备及其应用

基本信息

批准号：
18590005
负责人：
ABE Hitoshi
金额：
$ 2.53万
依托单位：
Okayama University
依托单位国家：
日本
项目类别：
Grant-in-Aid for Scientific Research (C)
财政年份：
2006
资助国家：
日本
起止时间：
2006 至 2007
项目状态：
已结题

项目摘要

Biaryl compounds are important building blocks for naturally occurring materials, and the methods for forming carbon-carbon bond between two aromatic rings have been developed for over 100 years. As a classical method, the Ullmann coupling has been a standard transformation to prepare biaryl molecules although this method often requires the vigorous reaction conditions. Additionally, in the Ullmann coupling, there are some difficulties for the synthesis of unsymmetrical biaryl molecules.For more convenient procedure, Suzuki-Miyaura coupling reaction has widely been utilized for the biaryl synthesis, as well as Stille coupling reaction. For these transformations, the functionalization on both of aromatic rings are necessary, i.e. halogenation on one aromatic ring, and the introduction of boron or tin atom on the other one. However, two aromatic rings, if they are linked with ester or amide group each other, can be coupled using Pd reagent without introduction of the functional group on one aromatic ring. Under such a concept, the intramolecular Pd-mediated biaryl coupling reactions have been developed to synthesize many polycyclic aromatic compounds including some natural products.

联芳基化合物是天然材料的重要组成部分，在两个芳香环之间形成碳-碳键的方法已经发展了100多年。乌尔曼偶联是制备联芳基分子的一种经典方法，但该方法往往需要较强的反应条件。此外，在乌尔曼偶联中，不对称联芳基分子的合成也存在一些困难。为了更方便地合成联芳基，Suzuki-Miyaura偶联反应和Stille偶联反应被广泛应用于联芳基的合成。对于这些转化，两个芳环上的功能化是必要的，即一个芳环上卤化，另一个上引入硼或锡原子。然而，如果两个芳香环彼此连接有酯或酰胺基团，则可以使用Pd试剂偶联，而无需在一个芳香环上引入官能团。在这一概念下，分子内pd介导的联芳基偶联反应被开发出来，合成了许多多环芳香族化合物，包括一些天然产物。