Alkylarylation of alkenes with arylsulfonylacetate as bifunctional reagent via photoredox radical addition/smiles rearrangement cascade

He, Chonglong; Wang, Yulong; Li, Quan-Xin; Yan, Zichen; Zhang, Keyuan; Ni, Shao-Fei; Duan, Xin-Hua; Liu, Le

doi:10.1016/j.cclet.2024.110253

Chinese Chemical Letters

2024

DOI: 10.1016/j.cclet.2024.110253

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Alkylarylation of alkenes with arylsulfonylacetate as bifunctional reagent via photoredox radical addition/smiles rearrangement cascade

Chonglong He,

Yulong Wang,

Quan-Xin Li

et al.

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2024

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Photoredox Catalyzed Conia-Ene-Type Cyclization/Smiles Rearrangement Cascade Reactions to Access Substituted Methylenecarbocycles

Zhang,

Jiang,

et al. 2024

Org. Lett.

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We report a novel visible-light-driven photoredox-catalyzed cascade reaction involving Conia-ene-type cyclization and Smiles rearrangement initiated from alkyne-tethered α-sulfonyl esters. This methodology not only facilitates the rapid synthesis of a broad spectrum of highly substituted methylenecarbocycles but also introduces a new mechanistic pathway with aryl group migration, surpassing the conventional 1,5-hydrogen shift typically observed in Conia-ene reactions.

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Photoredox Catalyzed Conia-Ene-Type Cyclization/Smiles Rearrangement Cascade Reactions to Access Substituted Methylenecarbocycles

Zhang,

Jiang,

et al. 2024

Org. Lett.

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Alkylarylation of alkenes with arylsulfonylacetate as bifunctional reagent via photoredox radical addition/smiles rearrangement cascade

Cited by 1 publication

References 67 publications

Photoredox Catalyzed Conia-Ene-Type Cyclization/Smiles Rearrangement Cascade Reactions to Access Substituted Methylenecarbocycles

Photoredox Catalyzed Conia-Ene-Type Cyclization/Smiles Rearrangement Cascade Reactions to Access Substituted Methylenecarbocycles

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