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Regioselective introduction of vinyl trifluoromethylthioether to remote unactivated C(sp3)—H bonds via radical translocation cascade

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Abstract

Described herein is an efficient protocol for the regioselective introduction of a vinyl trifluoromethylthioether to remote unactivated C(sp3)—H bonds. The cascade process involves the vinyl radical-mediated 1,5-hydrogen atom transfer (HAT) and remote vinyl migration. During the transformation, inert C—H and C—C bonds are consecutively cleaved under mild conditions. The reaction features good functional group tolerance, broad substrate scope, and high regio-/stereo-selectivity.

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Acknowledgements

This work was supported by Soochow University, the National Natural Science Foundation of China (21722205), the Project of Scientific and Technologic Infrastructure of Suzhou (SZS201708), and the Priority Academic Program Development of Jiangsu Higher Education Institutions.

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Authors and Affiliations

  1. Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Jiangsu, 215123, China

    Shuo Wu, Xinxin Wu, Zhen Wu & Chen Zhu

  2. Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Shanghai, 200032, China

    Chen Zhu

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  1. Shuo Wu
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  2. Xinxin Wu
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  3. Zhen Wu
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  4. Chen Zhu
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Correspondence to Chen Zhu.

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Regioselective Introduction of Vinyl Trifluoromethylthioether to Remote Unactivated C(sp3)-H Bonds via Radical Translocation Cascade

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Wu, S., Wu, X., Wu, Z. et al. Regioselective introduction of vinyl trifluoromethylthioether to remote unactivated C(sp3)—H bonds via radical translocation cascade. Sci. China Chem. 62, 1507–1511 (2019). https://doi.org/10.1007/s11426-019-9527-5

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  • DOI: https://doi.org/10.1007/s11426-019-9527-5

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