A Study on Visible Light-Driven Desulfonylative Cross-Coupling of Glycosyl Sulfones

• Author(s): Dr. N. Y. Badannavar
• Paper ID: 1703241
• Page: 680-688
• Published Date: 31-03-2022
• Published In: Iconic Research And Engineering Journals
• Publisher: IRE Journals
• e-ISSN: 2456-8880
• Volume/Issue: Volume 5 Issue 9 March-2022

Abstract

Visible light-driven desulfonylative cross-coupling reactions offer a powerful and sustainable strategy for the selective formation of carbon–carbon (C–C) bonds and the synthesis of glycosyl derivatives, including C-glycosides, in a highly efficient and environmentally friendly manner. In this study, we present a novel approach to the desulfonylative cross-coupling of glycosyl sulfones using visible light as the energy source. The reaction, carried out under mild, ambient temperature conditions, does not require transition metals or catalysts, thus significantly reducing the complexity and cost of the reaction. We investigate the reaction mechanism, demonstrating that the irradiation of glycosyl sulfones with visible light generates highly reactive glycosyl radicals, which can then undergo cross-coupling with various electrophiles, including aryl halides, vinyl compounds, and alkynes, to yield the desired C-glycoside products. The scope of the method was found to be broad, allowing for a variety of glycosyl donors and electrophilic partners to be successfully coupled, providing high yields and excellent stereoselectivity. Additionally, the reaction showed excellent functional group compatibility, tolerating the presence of hydroxyl, methoxy, and halogen groups on both the glycosyl donor and the electrophilic coupling partner. Notably, this visible light-driven method also outperforms traditional approaches that require transition metal catalysts, offering advantages such as increased atom economy, simplified work-up procedures, and higher environmental sustainability due to the elimination of toxic metal by-products. The developed strategy demonstrates the potential for large-scale applications, with successful reactions carried out at multi-gram scales, further emphasizing its practical value. Importantly, the method also exhibits high levels of regioselectivity in the C–C bond formation, which is crucial for the synthesis of complex glycosylated compounds. Overall, this study provides a highly efficient, green, and scalable strategy for the synthesis of glycosyl sulfones and opens up new possibilities for the development of light-driven reactions in glycosylation chemistry.

Keywords

Visible light-driven reactions, Desulfonylative cross-coupling, Glycosyl sulfones, C-glycosides, Green chemistry, Radical intermediates

Citations

IRE Journals:
Dr. N. Y. Badannavar "A Study on Visible Light-Driven Desulfonylative Cross-Coupling of Glycosyl Sulfones" Iconic Research And Engineering Journals Volume 5 Issue 9 2022 Page 680-688

IEEE:
Dr. N. Y. Badannavar "A Study on Visible Light-Driven Desulfonylative Cross-Coupling of Glycosyl Sulfones" Iconic Research And Engineering Journals, 5(9)