Citation: 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. doi: 10.6023/cjoc202005048 shu

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

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

Corresponding author: Li Qingjiang, liqingj3@mail.sysu.edu.cn
Received Date: 19 May 2020
Revised Date: 10 July 2020
Available Online: 22 July 2020
Fund Project: the Guangdong Provincial Key Laboratory of Chiral Molecule and Drug Discovery 2019B030301005the State Key Laboratory of Natural and Biomimetic Drugs, Peking University K20170210the Guangdong Basic and Applied Basic Research Foundation 2019A1515011322the National Natural Science Foundation of China 81930098Project 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)the Fundamental Research Funds for the Central Universities 19ykpy124

Figures(3)

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.
- photoisomerization,
- monofluorostilbenes,
- stereoselectivity,
- energy transfer
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