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

doi:10.6023/cjoc202005048

Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (10): 3314-3326.DOI: 10.6023/cjoc202005048 Previous Articles Next Articles

Special Issue: 有机光催化虚拟合辑；黄乃正院士七十华诞专辑

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^a, 林鹏鹏^a, 杨羚^a, 谭东航^a, 冯嗣欣^a, 王洪根^a, 李清江^a,b

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 发布日期:2020-07-23
通讯作者: 李清江 E-mail:liqingj3@mail.sysu.edu.cn
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.

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

Zhang Qi-Qi^a, Lin Peng-Peng^a, Yang Ling^a, Tan Dong-Hang^a, Feng Si-Xin^a, Wang Honggen^a, Li Qingjiang^a,b

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:2020-05-19 Revised:2020-07-10 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).

1. cjoc202005048.pdf(9867KB)

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

Cite this article

Zhang Qi-Qi, Lin Peng-Peng, Yang Ling, Tan Dong-Hang, Feng Si-Xin, Wang Honggen, Li Qingjiang. Visible-Light-Promoted Ir(III)-Catalyzed Z→E Isomerization of Monofluorostilbenes[J]. Chinese Journal of Organic Chemistry, 2020, 40(10): 3314-3326.

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可见光促进三价铱催化单氟均二苯乙烯Z→E异构化反应

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

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