α-Acyloxylation of Ketones/Cyclic Ethers Mediated by Hypervalent Iodine(III) Reagents as Oxidants and Nucleophilic Sources

Abstract

This study describes a catalyst-free α-acyloxylation of ketones and a KBr-mediated α-acyloxylation of cyclic ethers. These conversions are effectively mediated by hypervalent iodine(III) reagents serving dual roles as the oxidant and nucleophilic source. Consequently, esters are produced directly in moderate to excellent yields. The proposed method features good functional group compatibility, a broad substrate scope, and high synthetic efficiency and is remarkably environmentally friendly.

Metal- and light-free decarboxylative direct C–H alkylation of heteroarenes at room temperature

“…First, deprotonation of 2-nitropropane produces nitronate anion A ( A′ ) in the presence of DBU, which can react with HICs to form the relatively stable α-radical B via a single electron-transfer (SET) process. HICs are translated into iodanyl radical C , 13 which can undergo sequential cleavage of its I–O bond to provide the carboxyl radical D and iodobenzene. D can then generate the alkyl radical E with the release of CO 2 .…”