Journal
GREEN CHEMISTRY
Volume 24, Issue 10, Pages 4108-4118Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/d2gc00799a
Keywords
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Funding
- Hellenic Foundation for Research and Innovation (HFRI)
- Hellenic Foundation for Research and Innovation [655]
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In this study, a novel and sustainable light-driven method for synthesizing sulfoxides was developed and the impact of different wavelength irradiation on sulfide oxidation was investigated.
The sulfoxide moiety is recognized as one of the most important groups in organic and medicinal chemistry. Many efforts worldwide focus on developing novel and sustainable protocols, accessing sulfoxide-containing molecules. Photochemistry plays a unique role in sulfoxide synthesis, since this new emerging field, employing light as the energy source, is essential in developing novel and eco-friendly protocols. Herein, we report a novel, sustainable, light-driven protocol, where the impact of wavelength irradiation on sulfide aerobic photooxidation was examined. In this work, two different low-catalyst loading (0.05-0.5 mol%) protocols, utilizing anthraquinone as the photocatalyst (under CFL lamps or 427 nm irradiation) were developed and a catalyst-free protocol (under 370 nm irradiation) was also assessed. In addition, a broad scope of substrates was tested and extensive mechanistic studies were performed, in order to distinguish the mechanistic pathways that are followed in the different cases of aryl or alkyl sulfide oxidation under different wavelength irradiation. We also implemented our protocols towards the oxidation of several intermediates en route to Sulforaphane.
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