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

Jia-Li Sui; Xin-Qian Liu; Shun-Dan Li; Peng-Fei Huang; Yu Liu; Jin-Heng Li

doi:10.1002/cjoc.202400628

Chinese Journal of Chemistry ›› 2024, Vol. 42 ›› Issue (24) : 3373 -3378. DOI: 10.1002/cjoc.202400628

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

Jia-Li Sui ¹
, Xin-Qian Liu ¹
, Shun-Dan Li ¹
, Peng-Fei Huang ¹^,^†
, Yu Liu ¹^,^†
, Jin-Heng Li ²^,³^,⁴^,^†

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Abstract

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 (PPh ₃) 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.

Keywords

Photocatalysis / Cyclization / Nitrogen heterocycles / N-Hydroxyphthalimide esters / Phenanthridine / Alkylation / Radical reactions / Decarboxylation

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Jia-Li Sui, Xin-Qian Liu, Shun-Dan Li, Peng-Fei Huang, Yu Liu, Jin-Heng Li. Photochemical Decarboxylative Radical Alkylation/Cyclization Reaction to Fused Nitrogen Heterocycles by LiI/PPh₃ Catalysis. Chinese Journal of Chemistry, 2024, 42(24): 3373-3378 DOI:10.1002/cjoc.202400628