Metal‐Free Generation of Acyl Fluorides via Activation of Cyclopropyl Esters using a Hypervalent Iodine(III) Species and Selectfluor.

Abstract

An efficient method for the activation of non‐activated cyclopropyl esters is developed using a hypervalent iodine(III) species and Selectfluor for the generation of acyl fluoride intermediates. The reactive acyl fluoride intermediate is smoothly transformed into various functional groups such as amides, esters, thioesters, and ketones depending on the nucleophile used in the in‐situ transformation. Utilizing the oxidation process of an iodoarene by Selectfluor, the activation is improved from a stoichiometric to catalytic protocol. Furthermore, the activation is employed in the chemoselective activation of target cyclopropyl ester in the presence of other ester moieties.