Visible-Light Induced and Iron Peroxo-Promoted Radical Difunctionalization of Alkene for the Synthesis of β‑Ketosulfone and α‑Chloroketone

In this work, a switchable synthesis of β-ketosulfone and α-chloroketone through a radical difunctionalization of alkenes is reported. The transformation works well under iron peroxo species/photoredox dual catalysis and an open-flask atmosphere, and the reaction is highlighted with good yields and...

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Veröffentlicht in:Journal of organic chemistry 2025-01, Vol.90 (1), p.768-776
Hauptverfasser: Zhu, Xinyu, Bao, Chen, Zhang, Xingxian, Chen, Niuhai, Guan, Meng, Liao, Yuling Yu, Qiu, Guanyinsheng
Format: Artikel
Sprache:eng
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Zusammenfassung:In this work, a switchable synthesis of β-ketosulfone and α-chloroketone through a radical difunctionalization of alkenes is reported. The transformation works well under iron peroxo species/photoredox dual catalysis and an open-flask atmosphere, and the reaction is highlighted with good yields and a broad reaction scope. Mechanism studies show that the reaction is initiated by a formal [4 + 2] cyclization of the sulfonyl radical in a regioselective manner.
ISSN:0022-3263
1520-6904
1520-6904
DOI:10.1021/acs.joc.4c02720