Citation: Shan-Shan Li, Juan Luo, Shu-Nuo Liang, Dan-Na Chen, Li-Ning Chen, Cheng-Xue Pan, Peng-Ju Xia. Efficient and regioselective C=S bond difunctionalization through a three-component radical relay strategy[J]. Chinese Chemical Letters, ;2025, 36(6): 110424. doi: 10.1016/j.cclet.2024.110424 shu

Efficient and regioselective C=S bond difunctionalization through a three-component radical relay strategy

School of Chemistry and Pharmaceutical Sciences, Guangxi Normal University, Guilin 541004, China

xiapengju@gxnu.edu.cn

Received Date: 11 June 2024
Revised Date: 26 August 2024
Accepted Date: 6 September 2024
Available Online: 7 September 2024

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A novel photocatalytic energy transfer-driven radical relay strategy has been introduced for the chemo- and regioselective 1, 4-difunctionalization of carbon-sulfur double bonds. This represents the first instance of radical-mediated dual-functionalization of X-Y type unsaturated bonds, enabling the synthesis of complex linear molecules with CO, CN, and C-S bonds in a single operation. The method surpasses traditional approaches by avoiding the need for thiourea intermediates and the harsh conditions typically associated with them. The developed strategy exemplifies versatility, being applicable to 1, 4-oxyamination, 1, 4-diamination, and 1, 4-sulfonamination reactions, and has demonstrated compatibility with over 60 different substrates. The research also elucidates the role of electronic complementarity between radicals and receptors in achieving high selectivity in 1, 4-difunctionalization reactions. This study significantly advances the field of bifunctionalization and remote difunctionalization reactions, with profound implications for the development of pharmaceuticals and materials science.
- Radical relay,
- Selective 1, 4-difunctionalization,
- Multicomponent reactions,
- Isothiocyanates,
- C=S bonds
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