Photochemical Radical Cascade 6-endo Cyclization of Dienes with α-Carbonyl Bromides for the Synthesis of Six-Membered Benzo-Fused Lactams

Jia-Li Sui , Yang Guo , Bi-Quan Xiong , Ke-Wen Tang , Peng-Fei Huang , Yu Liu , Jin-Heng Li

Chinese Journal of Chemistry ›› 2024, Vol. 42 ›› Issue (19) : 2323 -2328.

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Chinese Journal of Chemistry ›› 2024, Vol. 42 ›› Issue (19) : 2323 -2328. DOI: 10.1002/cjoc.202400310
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Photochemical Radical Cascade 6-endo Cyclization of Dienes with α-Carbonyl Bromides for the Synthesis of Six-Membered Benzo-Fused Lactams

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Abstract

A novel visible-light-induced radical cascade 6- endo cyclization of dienes ( N-(2-vinylphenyl)acryl amides) is developed utilizing α-carbonyl bromides as alkyl reagents. This approach affords an efficient way for synthesizing six-membered benzo-fused lactam derivatives with chemo- and regio-selectivity and good functional group tolerance. Primary, secondary, and tertiary bromides are well-compatible with this cascade cyclization reaction.

Keywords

Visible-light-induced reaction / Cyclization / Transition-metal-free / Nitrogen heterocycles / α-Carbonyl bromides / Lactams / Alkylation / Radical reactions / Reduction

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Jia-Li Sui, Yang Guo, Bi-Quan Xiong, Ke-Wen Tang, Peng-Fei Huang, Yu Liu, Jin-Heng Li. Photochemical Radical Cascade 6-endo Cyclization of Dienes with α-Carbonyl Bromides for the Synthesis of Six-Membered Benzo-Fused Lactams. Chinese Journal of Chemistry, 2024, 42(19): 2323-2328 DOI:10.1002/cjoc.202400310

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2024 SIOC, CAS, Shanghai, & WILEY-VCH GmbH

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