Citation: Chonglong He, Yulong Wang, Quan-Xin Li, Zichen Yan, Keyuan Zhang, Shao-Fei Ni, Xin-Hua Duan, Le Liu. Alkylarylation of alkenes with arylsulfonylacetate as bifunctional reagent via photoredox radical addition/Smiles rearrangement cascade[J]. Chinese Chemical Letters, ;2025, 36(5): 110253. doi: 10.1016/j.cclet.2024.110253 shu

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

Chonglong He ^a ,
Yulong Wang ^a ,
Quan-Xin Li ^b ,
Zichen Yan ^a ,
Keyuan Zhang ^a ,
Shao-Fei Ni ^b ,
Xin-Hua Duan ^a ,
Le Liu ^{a, *,}

a.
School of Chemistry, Engineering Research Center of Energy Storage Materials and Devices, Ministry of Education, Xi’an Key Laboratory of Sustainable Energy Material Chemistry, Xi’an Jiaotong University, Xi’an 710049, China
b.
Department of Chemistry, Key Laboratory for Preparation and Application of Ordered Structural Materials of Guangdong Province, Shantou University, Shantou 515063, China

le.liu@xjtu.edu.cn

Received Date: 20 May 2024
Revised Date: 8 July 2024
Accepted Date: 15 July 2024
Available Online: 15 July 2024

Figures(7)

The radical difunctionalization of alkenes with sulfonyl bifunctional represents a powerful and straightforward approach to access functionalized alkane derivatives. However, both the mechanistic activation mode and the substrate scopes of this type of radical difunctionalizations are still limited. We demonstrate herein a modular photoredox strategy for the difunctionalization of alkenes, employing arylsulfonyl acetate as the bifunctional reagent. This approach involves a radical addition/Smiles rearrangement cascade process, offering a robust alternative for the synthesis of valuable γ,γ-diaryl and γ-aryl esters. A complementary oxidative bifunctional reagents activation mode is identified to govern the radical cascade reactions, facilitating the simultaneous incorporation of aryl and carboxylate-bearing alkyl groups into the alkenes with excellent diastereoselectivity. Noteworthy features of this method include mild reaction conditions, organophotocatalysis, high atom- and step-economy, excellent functional group compatibility and great structural diversity.
- Radical difunctionalization,
- Bifunctional reagents,
- Smiles rearrangement,
- Photoredox,
- γ,γ-Diaryl and γ-aryl ester
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