Radical cascade cyclization of 1,<i>n</i>-enynes under photo/electrochemical conditions

Cai, Zhenzhi; Trienes, Sven; Liu, Kairui; Ackermann, Lutz; Zhang, Yan

doi:10.1039/d3qo01482g

Org. Chem. Front.

2023

DOI: 10.1039/d3qo01482g

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Radical cascade cyclization of 1,n-enynes under photo/electrochemical conditions

Zhenzhi Cai,

Sven Trienes,

Kairui Liu

et al.

Abstract: During the past decade, photo- and electrochemical reactions proceeding via single-electron-transfer (SET) triggered radical pathways have emerged as an indispensable strategy for the efficient formation of chemical bonds. Especially, radical...

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2024

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Cited by 18 publications

(1 citation statement)

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“…9 Very recently, the groups of Studer/Xuan, and Zhang separately summarized a wide range of efficient cyclization reactions of 1, n -enynes reported by numerous researchers, which result in various heterocycles. 10 Meanwhile, Li et al reported a radical bicyclization of 1,7-enynes with tert -butyl nitrite to access nitro-containing pyrrolo[4,3,2- de ]quinolinones. 11 Wei and coworkers developed a radical bicyclization of 1,6-enynes with sulfonyl hydrazides to result in sulfone-featured polyheterocycles.…”

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confidence: 99%

Metal-free radical bicyclization/chloroalkylarylation of 1,6-enynes with chloroalkanes

Zhou,

Li,

Yan

et al. 2024

Chem. Commun.

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mentioning

confidence: 99%

Metal-free radical bicyclization/chloroalkylarylation of 1,6-enynes with chloroalkanes

Zhou,

Li,

Yan

et al. 2024

Chem. Commun.

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Radical Carbocyclization Intercepted Reductive C−C Bond Formation Between 1,n‐Enynes or Dienes and Electron‐Poor Olefins/Alkynes

Hazra,

Patel,

Saha

2024

Adv Synth Catal

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Metal hydride catalyzed hydrogen atom transfer (MHAT) reaction of 1,6‐enyne and electron‐poor alkene progresses through a radical cascade, involving ene‐yne cyclization and exocyclic C‐C bond formation superseding the direct reductive olefin cross‐coupling; which is realized in the current study. The generality of this reaction manifold is demonstrated with a range of functionalized 1,6‐enyne and dienes and involving structurally distinct electron‐poor olefins and alkynes as partners. Current work unveils a merger of MHAT‐based olefin‐hydro functionalization with radical ene‐one cyclization.

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Boryl Radical as a Catalyst in Enabling Intra‐ and Intermolecular Cascade Radical Cyclization Reactions: Construction of Polycyclic Molecules

Wang,

Lin Phang,

et al. 2024

Angewandte Chemie

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Cascade radical cyclization constitutes an atom‐ and step‐economic route for rapid assembly of polycyclic molecular skeletons. Although an array of redox‐active metal catalysts has recently shown robust applications in enabling various catalytic cascade radical processes, the use of free organic radical as the catalyst, which is capable of triggering strategically distinct cascades, has rarely been developed. Here, we disclosed that the benzimidazolium‐based N‐heterocyclic carbene (NHC)‐boryl radical is capable of catalyzing cascade cyclization reactions in both intra‐ and intermolecular pathways, assembling [5,5] fused bicyclic and [6,6,6] fused tricyclic molecules, respectively. The catalytic reactions start with the chemo‐ and regioselective addition of the boryl radical catalyst to a tethered alkene or alkyne moiety, followed by either an intramolecular formal [3+2] or an intermolecular [2+2+2] cycloaddition process to construct bicyclo[3.3.0]octane or tetrahydrophenanthridine skeletons, respectively. Eventually, a β‐elimination occurs to release the boryl radical catalyst, completing a catalytic cycle. High to excellent diastereoselectivity is achieved in both catalytic reactions under substrate control.

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Radical cascade cyclization of 1,n-enynes under photo/electrochemical conditions

Abstract: During the past decade, photo- and electrochemical reactions proceeding via single-electron-transfer (SET) triggered radical pathways have emerged as an indispensable strategy for the efficient formation of chemical bonds. Especially, radical...

Cited by 18 publications

References 84 publications

Metal-free radical bicyclization/chloroalkylarylation of 1,6-enynes with chloroalkanes

Metal-free radical bicyclization/chloroalkylarylation of 1,6-enynes with chloroalkanes

Radical Carbocyclization Intercepted Reductive C−C Bond Formation Between 1,n‐Enynes or Dienes and Electron‐Poor Olefins/Alkynes

Boryl Radical as a Catalyst in Enabling Intra‐ and Intermolecular Cascade Radical Cyclization Reactions: Construction of Polycyclic Molecules

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