Modular synthesis of 1,4-diketones through regioselective bis-acylation of olefins by merging NHC and photoredox catalysis |
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| Affiliation: | 1. Antibiotics Research and Re-evaluation Key Laboratory of Sichuan Province, Sichuan Industrial Institute of Antibiotics, School of Pharmacy, Chengdu University, Chengdu 610106, China;2. State Key Laboratory of Southwestern Chinese Medicine Resources, School of Pharmacy, Chengdu University of Traditional Chinese Medicine, Chengdu 611137, China;1. Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, CAS Research/Education Center for Excellence in Molecular Sciences, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China;2. University of Chinese Academy of Sciences, Beijing 100049, China;1. Sichuan Research Center for Drug Precision Industrial Technology, West China School of Pharmacy, Sichuan University, Chengdu 610041, China;2. Engineering Center of Catalysis and Synthesis for Chiral Molecules, Department of Chemistry, Fudan University, Shanghai 200433, China;3. Shanghai Engineering Center of Industrial Asymmetric Catalysis for Chiral Drugs, Shanghai 200433, China;1. State Key Laboratory of Pulp and Paper Engineering, South China University of Technology, Guangzhou 510641, China;2. School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou 510641, China;1. Department of Chemistry and Innovation Center of Pesticide Research, China Agricultural University, Beijing 100193, China;2. College of Public Health, Zhengzhou University, Zhengzhou 450001, China;1. College of Chemistry and Pharmaceutical Sciences, Qingdao Agricultural University, Qingdao 266109, China;2. National Engineering Research Center of Low-Carbon Processing and Utilization of Forest Biomass, Nanjing Forestry University, Nanjing 210037, China;1. Key Laboratory of Jiangxi Province for Persistent Pollutants Control and Resources Recycle, Nanchang Hangkong University, Nanchang 330063, China;2. State Key Laboratory Base of Eco-Chemical Engineering, College of Chemical Engineering, Qingdao University of Science and Technology, Qingdao 266042, China;3. State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, China;4. School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang 453007, China |
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| Abstract: | Efficient and modular synthesis of structurally diverse 1,4-diketones from readily available building blocks represents an essential but challenging task in organic chemistry. Herein, we report a multi-component, regioselective bis-acylation of olefins by merging NHC organocatalysis and photoredox catalysis. With this protocol, a broad range of 1,4-diketones could be rapidly assembled using bench-stable feedstock materials. The robustness of this method was further evaluated by sensitivity screening, and good reproductivity was observed. Moreover, the diketone products could be readily converted into functionalized heterocycles, such as multi-substituted furan, pyrrole, and pyridazine. Mechanistic investigations shed light on the NHC and photoredox dual catalytic radical reaction mechanism. |
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