Uracil-BX: Bench-Stable Cyclic Hypervalent Iodine Reagents for Umpolung Functionalization.

Org Lett

Department of Chemistry, Jadavpur University, 188, Raja S. C. Mallick Road, Jadavpur, Kolkata, West Bengal 700032, India.

Published: August 2025


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Article Abstract

Herein, we report a straightforward synthetic protocol to afford a series of novel Uracil-based bench-stable cyclic hypervalent iodine reagents, Uracil-benziodoxolone ( Uracil-BX). The 3c-4e weak bonds of these hitherto unreported hypervalent iodine reagents were also synthetically exploited for sulfenylation and amination at the C5 position of Uracil via an umpolung strategy. Metal-free approaches for this functionalization at the C5 position lead to various interesting Uracil derivatives that resemble medicinally important molecules.

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http://dx.doi.org/10.1021/acs.orglett.5c02248DOI Listing

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