Aerobic Oxidative Sulfenylation of Pyrazolones and Pyrazoles Catalyzed by Metal-Free Flavin–Iodine Catalysis

Two-component metal-free catalytic oxidative sulfenylation of pyrazolones with thiols has been achieved using the biomimetic flavin and iodine. The methodology is mild and eco-friendly, proceeds in the presence of air or molecular oxygen (1 atm) as the sole sacrificial reagent, and generates water a...

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Veröffentlicht in:Journal of organic chemistry 2019-11, Vol.84 (22), p.14980-14986
Hauptverfasser: Tanimoto, Kazumasa, Ohkado, Ryoma, Iida, Hiroki
Format: Artikel
Sprache:eng
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Zusammenfassung:Two-component metal-free catalytic oxidative sulfenylation of pyrazolones with thiols has been achieved using the biomimetic flavin and iodine. The methodology is mild and eco-friendly, proceeds in the presence of air or molecular oxygen (1 atm) as the sole sacrificial reagent, and generates water as the only byproduct. The methodology was also extended to the sulfenylation of pyrazoles and electron-rich benzenes and afforded a series of thioethers in good yields.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.9b02422