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Radical Functionalization of Thioglycosides in Aqueous Medium

preprint
submitted on 07.04.2020 and posted on 09.04.2020 by Sarbjeet Kaur, dominic luciano, gaoyuan zhao, Ting Wang

A visible-light-mediated thiol-ene reaction is successfully operated in aqueous medium. Organic photoredox catalyst (9-mesityl-10-methylacridinum tetrafluoroborate) is used to initiate the radical process to generate thiyl radicals upon light irradiation. Two reaction pathways are discovered in different aqueous buffer system. Thiol-ene adduct is preferred in acidity reaction medium; while disulfide formation is found to be favored in basic reaction medium. Moreover, a visible-light-mediated modified Danishefsky-Wan desulfurization is used to convert thioglycoside to highly substituted tetrahydropyran ring.

History

Email Address of Submitting Author

twang3@albany.edu

Institution

State University of New York at Albany

Country

United States

ORCID For Submitting Author

0000-0001-7630-4148

Declaration of Conflict of Interest

no conflict of interest

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