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2020 , Vol. 40 >Issue 10: 3314 - 3326

DOI: https://doi.org/10.6023/cjoc202005048

研究论文

可见光促进三价铱催化单氟均二苯乙烯Z→E异构化反应

  • 张其奇 ,
  • 林鹏鹏 ,
  • 杨羚 ,
  • 谭东航 ,
  • 冯嗣欣 ,
  • 王洪根 ,
  • 李清江
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  • a 中山大学药学院 广东省手性分子与药物发现重点实验室 广州 510006;
    b 北京大学 天然药物及仿生药物国家重点实验室 北京 100191

收稿日期: 2020-05-19

  修回日期: 2020-07-10

  网络出版日期: 2020-07-23

基金资助

广东省基础与应用基础研究基金（No.2019A1515011322）、中央高校基本科研业务费专项资金（No.19ykpy124）、国家自然科学基金（No.81930098）、广东省手性分子与药物发现重点实验室（No.2019B030301005）、北京大学天然药物及仿生药物国家重点实验室开放基金（No.K20170210）资助项目.

收起

Visible-Light-Promoted Ir(III)-Catalyzed Z→E Isomerization of Monofluorostilbenes

  • Zhang Qi-Qi ,
  • Lin Peng-Peng ,
  • Yang Ling ,
  • Tan Dong-Hang ,
  • Feng Si-Xin ,
  • Wang Honggen ,
  • Li Qingjiang
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  • a Guangdong Provincial Key Laboratory of Chiral Molecule and Drug Discovery, School of Pharmaceutical Sciences, Sun Yat-sen University, Guangzhou 510006;
    b State Key Laboratory of Natural and Biomimetic Drugs, Peking University, Beijing 100191

Received date: 2020-05-19

  Revised date: 2020-07-10

  Online published: 2020-07-23

Supported by

Project supported by the Guangdong Basic and Applied Basic Research Foundation (No. 2019A1515011322), the Fundamental Research Funds for the Central Universities (No. 19ykpy124), the National Natural Science Foundation of China (No. 81930098), the Guangdong Provincial Key Laboratory of Chiral Molecule and Drug Discovery (No. 2019B030301005), and the State Key Laboratory of Natural and Biomimetic Drugs, Peking University (No. K20170210).

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摘要

报道了一种可见光（蓝光）促进单氟均二苯乙烯类底物立体异构化反应.该反应使用三价铱络合物为催化剂，通过选择性能量转移途径，提供了一类热力学上相对不稳定E式单氟均二苯乙烯类化合物快速合成方法.该催化体系条件温和，具有广泛的官能团兼容性和良好的底物适用范围，以及实用的合成效率（产率高达96%， E：Z比高达91：9）.此外，利用该方法还快速合成了DMU-212分子的顺式单氟衍生物，初步验证了方法的实用性.

关键词： 光异构化; 单氟均二苯乙烯; 立体选择性; 能量转移

本文引用格式

张其奇 , 林鹏鹏 , 杨羚 , 谭东航 , 冯嗣欣 , 王洪根 , 李清江 . 可见光促进三价铱催化单氟均二苯乙烯Z→E异构化反应[J]. 有机化学, 2020 , 40(10) : 3314 -3326 . DOI: 10.6023/cjoc202005048

Abstract

A photocatalytic Z to E isomerization of monofluorostilbenes in the presence of visible light (blue LEDs) has been developed. The transformation, which proceeds through a selective energy transfer pathway with Ir(Ⅲ) complex, offers facile access to thermodynamically less stable E-monofluoroalkenes with synthetically useful efficiency (up to 96% yield, up to 91:9 E:Z). Mild reaction conditions, good functional groups tolerance, and broad substrate scope were observed. Furthermore, the synthetic utility of this method is demonstrated by the rapid synthesis of monofluorinated cis-DMU-212 analogue E-30.

Key words： photoisomerization; monofluorostilbenes; stereoselectivity; energy transfer

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