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2024 , Vol. 44 >Issue 12: 3771 - 3783

DOI: https://doi.org/10.6023/cjoc202404004

研究论文

钯催化C—P键偶联反应高效构建手性联二萘基磷杂七元环化合物

  • 王崔颖 ,
  • 张颖 ,
  • 郑家练 ,
  • 袁佳 ,
  • 孟思璇 ,
  • 陈建 ,
  • 余广鳌
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  • a 武汉纺织大学 省部共建纺织新材料与先进加工技术国家重点实验室 武汉 430200
    b 华中师范大学化学学院 绿色农药全国重点实验室 传感技术与健康国家级智能生物国际联合研究中心 武汉 430079

收稿日期: 2024-04-02

  修回日期: 2024-05-16

  网络出版日期: 2024-06-24

基金资助

国家自然科学基金(22371084); 国家自然科学基金(21072071); 国家自然科学基金(21472060); 国家自然科学基金(21772058); 高等学校学科创新引智计划(111计划); 高等学校学科创新引智计划(B17019); 华中师范大学中央高校基本科研业务费专项资金(CCNU17CG0011); 华中师范大学中央高校基本科研业务费专项资金(CCNU17KYZHSY07); 华中师范大学中央高校基本科研业务费专项资金(CCNU18KYZHSY06)

收起

Efficient Construction of Chiral Binaphthalene-Core Phosphepine Compounds Using Palladium-Catalyzed C—P Coupling Reactions

  • Cuiying Wang ,
  • Ying Zhang ,
  • Jia-Lian Zheng ,
  • Jia Yuan ,
  • Sixuan Meng ,
  • Jian Chen ,
  • Guang-Ao Yu
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  • a State Key Laboratory of New Textile Materials and Advanced Processing Technologies, Wuhan Textile University, Wuhan 430200
    b International Joint Research Center for Intelligent Biosensor Technology and Health, National Key Laboratory of Green Pesticides, College of Chemistry, Central China Normal University, Wuhan 430079
*Corresponding authors. E-mail:;

Received date: 2024-04-02

  Revised date: 2024-05-16

  Online published: 2024-06-24

Supported by

the National Natural Science Foundation of China(22371084); the National Natural Science Foundation of China(21072071); the National Natural Science Foundation of China(21472060); the National Natural Science Foundation of China(21772058); Programme of Introducing Talents of Discipline to Universities(111 Project); Programme of Introducing Talents of Discipline to Universities(B17019); Self-Determined Research Funds of Central China Normal University from the Colleges’ Basic Research and Operation of Ministry of Education(CCNU17CG0011); Self-Determined Research Funds of Central China Normal University from the Colleges’ Basic Research and Operation of Ministry of Education(CCNU17KYZHSY07); Self-Determined Research Funds of Central China Normal University from the Colleges’ Basic Research and Operation of Ministry of Education(CCNU18KYZHSY06)

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摘要

在不对称催化合成反应中, 轴手性联二萘基磷杂七元环化合物是一类重要的有机催化剂和配体. 受限于合成方法, 该类化合物的种类少, 应用范围小. 开发了一种简单高效的钯催化C—P键偶联反应, 采用Pd(OAc)2/dippf催化光学纯度的(R)-1和卤代(杂)芳烃反应, 以中等至良好的收率(40%~92%)和高的ee值(90%~99% ee)获得了一系列轴手性联二萘基磷杂七元环化合物.

关键词： 钯催化; 轴手性; 联萘; C—P键偶联反应

本文引用格式

王崔颖 , 张颖 , 郑家练 , 袁佳 , 孟思璇 , 陈建 , 余广鳌 . 钯催化C—P键偶联反应高效构建手性联二萘基磷杂七元环化合物[J]. 有机化学, 2024 , 44(12) : 3771 -3783 . DOI: 10.6023/cjoc202404004

Abstract

Binaphthalene-core phosphepine compounds with axial chirality belong to an important class of organocatalysts and ligands used in catalytic asymmetric synthesis. However, the number and application of these compounds have been limited due to the lack of efficient synthetic methods currently available to researchers. Herein, a simple and efficient palladium-catalyzed C—P cross-coupling reaction of enantiopure (R)-1 with a variety of aryl and heteroaryl halides is reported. The reaction provides access to a series of chiral binaphthalene-core phosphepine compounds using Pd(OAc)2/dippf as a catalyst, which allows most products to be formed in moderate to high yields (40%~92%) with excellent ee values (90%~99% ee).

Key words： Pd catalysis; chiral axially; binaphthalene; C—P coupling reactions

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