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Photoredox catalytic alkylarylation of alkynes with arylsulfonylacetate as bifunctional reagent

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Abstract

Difunctionalization of alkynes represents a powerful and straightforward approach to the synthesis of complex molecules. However, the radical difunctionalization of alkynes mediated by bifunctional reagents remains challenging and underexplored, despite significant progress having been made in alkene difunctionalization. Here, we report a novel arylsulfonylacetate skeleton in which aryl rings are attached to acetates through SO2, serving as a powerful bifunctional reagent for the alkylarylation of alkynes via vinyl-radical intermediate under photoredox conditions. This modular bifunctional reagent enables the simultaneous incorporation of a wide range of functional groups, including (hetero)aryl ring and alkyl carboxylate into alkynes, resulting in synthetically valuable all-carbon tetrasubstituted alkene derivatives. This transformation is distinguished by its redox-neutral nature, readily accessible starting materials, compatibility with diverse functional groups and its capacity to facilitate convergent synthesis. The utility of this approach was further demonstrated by the late-stage functionalization of complex molecules and the preparation of fluorescent molecules and anti-cancer drugs.

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Acknowledgements

This work was supported by the National Natural Science Foundation of China (21901199) and Xi’an Jiaotong University (7121192002).

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Authors and Affiliations

  1. 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

    Chonglong He, Min Wang, Yulong Wang, Lirong Zhao, Youkang Zhou, Keyuan Zhang, Shenyu Shen, Yaqiong Su, Xin-Hua Duan & Le Liu

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  1. Chonglong He
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  2. Min Wang
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Correspondence to Le Liu.

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Supporting information The supporting information is available online at chem.scichina.com and link.springer.com/journal/11426. The supporting materials are published as submitted, without typesetting or editing. The responsibility for scientific accuracy and content remains entirely with the authors.

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He, C., Wang, M., Wang, Y. et al. Photoredox catalytic alkylarylation of alkynes with arylsulfonylacetate as bifunctional reagent. Sci. China Chem. (2024). https://doi.org/10.1007/s11426-023-1930-6

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