Pd(II)-Catalyzed Selective [4+2] Benzannulations of Pyridones with Alkenes: Diversity-Oriented Synthesis of a Novel Fluorescent Quinolinone
Yiwei Xu
Key Laboratory of Xin′an Medicine, Ministry of Education, Anhui University of Chinese Medicine, Hefei, Anhui, 230038 China
Search for more papers by this authorYuanyuan Wang
Key Laboratory of Xin′an Medicine, Ministry of Education, Anhui University of Chinese Medicine, Hefei, Anhui, 230038 China
Search for more papers by this authorJing Li
Key Laboratory of Xin′an Medicine, Ministry of Education, Anhui University of Chinese Medicine, Hefei, Anhui, 230038 China
Search for more papers by this authorJinxiang Ye
Key Laboratory of Xin′an Medicine, Ministry of Education, Anhui University of Chinese Medicine, Hefei, Anhui, 230038 China
Search for more papers by this authorCorresponding Author
Hui Miao
Anhui Province Key Laboratory of Environmental Hormone and Reproduction, School of Biological and Food Engineering, Fuyang Normal University, Fuyang, Anhui, 236037 China
E-mail: [email protected]; [email protected]; [email protected]Search for more papers by this authorCorresponding Author
Qianwen Gao
College of Chemistry and Chemical Engineering, State Key Laboratory of Chemo/Biosensing and Chemometrics, Advanced Catalytic Engineering Research Center of the Ministry of Education, Hunan University, Changsha, Hunan, 410082 China
E-mail: [email protected]; [email protected]; [email protected]Search for more papers by this authorCorresponding Author
Chenggui Wu
Key Laboratory of Xin′an Medicine, Ministry of Education, Anhui University of Chinese Medicine, Hefei, Anhui, 230038 China
Anhui Province Key Laboratory of Environmental Hormone and Reproduction, School of Biological and Food Engineering, Fuyang Normal University, Fuyang, Anhui, 236037 China
E-mail: [email protected]; [email protected]; [email protected]Search for more papers by this authorYiwei Xu
Key Laboratory of Xin′an Medicine, Ministry of Education, Anhui University of Chinese Medicine, Hefei, Anhui, 230038 China
Search for more papers by this authorYuanyuan Wang
Key Laboratory of Xin′an Medicine, Ministry of Education, Anhui University of Chinese Medicine, Hefei, Anhui, 230038 China
Search for more papers by this authorJing Li
Key Laboratory of Xin′an Medicine, Ministry of Education, Anhui University of Chinese Medicine, Hefei, Anhui, 230038 China
Search for more papers by this authorJinxiang Ye
Key Laboratory of Xin′an Medicine, Ministry of Education, Anhui University of Chinese Medicine, Hefei, Anhui, 230038 China
Search for more papers by this authorCorresponding Author
Hui Miao
Anhui Province Key Laboratory of Environmental Hormone and Reproduction, School of Biological and Food Engineering, Fuyang Normal University, Fuyang, Anhui, 236037 China
E-mail: [email protected]; [email protected]; [email protected]Search for more papers by this authorCorresponding Author
Qianwen Gao
College of Chemistry and Chemical Engineering, State Key Laboratory of Chemo/Biosensing and Chemometrics, Advanced Catalytic Engineering Research Center of the Ministry of Education, Hunan University, Changsha, Hunan, 410082 China
E-mail: [email protected]; [email protected]; [email protected]Search for more papers by this authorCorresponding Author
Chenggui Wu
Key Laboratory of Xin′an Medicine, Ministry of Education, Anhui University of Chinese Medicine, Hefei, Anhui, 230038 China
Anhui Province Key Laboratory of Environmental Hormone and Reproduction, School of Biological and Food Engineering, Fuyang Normal University, Fuyang, Anhui, 236037 China
E-mail: [email protected]; [email protected]; [email protected]Search for more papers by this authorComprehensive Summary
Herein, an intermolecular palladium(II)-catalyzed regioselective [4+2] benzannulation reaction capable of converting 2-pyridones into quinolinones was developed using electron-deficient alkenes as two-carbon units. An examination of the reaction mechanism indicated that the extension from 2-pyridone to quinolinone was likely facilitated through a series of sequential C—H activation reactions or 6π electrocyclization, culminating in dehydrogenative aromatization. This method of diversity-oriented synthesis of quinolinone derivatives is characterized by a broad substrate scope, atom economy, and excellent chemical selectivity. In addition, these quinolinone derivatives exhibit fluorescent absorption within the visible-light spectrum, which makes them suitable candidates for the development of innovative fluorescent probes.
Supporting Information
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Appendix S1: Supporting Information |
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