Photo-triggered Intramolecular Radical Tandem Regioselective Alkylation/Cyclization of 1,6-Dienes with Redox-Active Esters Enabled by an EDA Complex |
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Authors: | Bin Sun Lan Ling Xiaohui Zhuang Lulu Yang Jieli Yin Can Jin |
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Institution: | 1. Collaborative Innovation Center of Yangtze River Delta Region Green Pharmaceuticals, Zhejiang University of Technology, Hangzhou, Zhejiang, 310014 China;2. College of Pharmaceutical Sciences, Zhejiang University of Technology, Hangzhou, Zhejiang, 310014 China |
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Abstract: | A photocatalyst- and metal-free radical tandem alkylation/cyclization between 1,6-dienes and redox-active esters has been developed, affording a series of N-aryl pyrrolidine-2-ones in moderate to good yields. The transformation is driven by the formation of an electron-donor-acceptor (EDA) complex and a subsequent single electron transfer (SET) process. This photocatalyst-free protocol features excellent regioselectivity, mild conditions and broad substrate scope, providing a facile access to 3-alkyl-3,4-dimethyl-1-phenylpyrrolidin-2-one.![image](/cms/asset/4ebcf094-ca07-4d92-8f6f-0b593a23c551/cjoc202200516-gra-0001.png) |
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Keywords: | Alkylation Cyclization EDA Complex Pyrrolidone Photocatalysis |
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