Volume 42, Issue 24 pp. 3373-3378
Concise Report

Photochemical Decarboxylative Radical Alkylation/Cyclization Reaction to Fused Nitrogen Heterocycles by LiI/PPh3 Catalysis

Jia-Li Sui

Jia-Li Sui

Department of Chemistry and Chemical Engineering, Hunan Institute of Science and Technology, Yueyang, Hunan, 414006 China

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Xin-Qian Liu

Xin-Qian Liu

Department of Chemistry and Chemical Engineering, Hunan Institute of Science and Technology, Yueyang, Hunan, 414006 China

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Shun-Dan Li

Shun-Dan Li

Department of Chemistry and Chemical Engineering, Hunan Institute of Science and Technology, Yueyang, Hunan, 414006 China

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Peng-Fei Huang

Corresponding Author

Peng-Fei Huang

Department of Chemistry and Chemical Engineering, Hunan Institute of Science and Technology, Yueyang, Hunan, 414006 China

E-mail: [email protected]; [email protected]; [email protected]Search for more papers by this author
Yu Liu

Corresponding Author

Yu Liu

Department of Chemistry and Chemical Engineering, Hunan Institute of Science and Technology, Yueyang, Hunan, 414006 China

E-mail: [email protected]; [email protected]; [email protected]Search for more papers by this author
Jin-Heng Li

Corresponding Author

Jin-Heng Li

State Key Laboratory Base of Eco-Chemical Engineering, College of Chemical Engineering, Qingdao University of Science and Technology, Qingdao, Shandong, 266042 China

State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou, Gansu, 730000 China

School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, Henan, 453007 China

E-mail: [email protected]; [email protected]; [email protected]Search for more papers by this author
First published: 10 September 2024
Citations: 8

Comprehensive Summary

A visible-light-induced decarboxylative radical cascade cyclization reaction between N-(2-cyanoaryl)-acrylamides and alkyl N-(acyloxy)phthalimide (NHPI esters) for the construction of phenanthridine derivatives has been developed. This approach utilizes lithium iodide (LiI) and triphenylphosphine (PPh3) as the redox catalysts and the alkyl radical is produced through the photoactivation of the electron donor-acceptor (EDA) complex. A series of primary, secondary, and tertiary alkyl-substituted phenanthridines are prepared in up to 82% yield without transition-metal catalysts, chemical oxidants, or metal-/organic dye-based photocatalysts.

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