Hypervalent Iodine Fluorination for Preparing Alkyl Fluorides (Stoichiometrically and Catalytically)

Excerpt

Fluorinated hypervalent iodine (III) reagents are a century-old class of compounds undergoing a resurgence over the past few decades. The renewed interest in these compounds stems from their ability to transfer fluorine to Lewis basic reagents as though they were a source of fluoronium “F⁺” ion. The purpose of this chapter is to introduce the reader to this growing field of fluorination chemistry by illustrating key trends and reactivity patterns, from the first synthesis of the reagent to the most recent advancements in catalytic asymmetric fluorinations [1]. The discussion will follow the chemistry of two classes of fluorinated hypervalent iodine (III) compounds, the (difluoroiodo)arenes (1) and the fluorinated iodobenzoxole (2) (Fig. 1). While this is intended to be comprehensive, the focus will be on discussing the differing reactivity patterns induced by these compounds, as opposed to presenting an exhaustive list of all the work.

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