Using Iron amides as Basic Reagents for Fluoroarene Metalation

Abstract

Fluoroarenes are important motifs in modern synthesis, yet regioselective C–H functionalization while preserving strong C–F bonds remains a significant challenge. Building on recent studies from our group, here we describe the potential of iron(II) amides to selectively promote regioselective mono- and di-ferration of a diverse range of fluoroaromatic substrates under mild conditions via Fe(II)–H exchange. Two alternative strategies are presented which include the use of a sodium ferrate which switches on heterobimetallic cooperation; and the development of a super basic iron amide containing TMP (2,2,6,6-tetramethylpiperidide) groups which allow for the efficient ferration of fluoroarenes under mild reaction conditions.