Abstract
Hypervalent iodine compounds are a widely used class of metal-free oxidants that find application in organic synthesis. Due to the homologous reactivity of hypervalent iodine and many transition metals oxidative addition, ligand exchange, and reductive elimination can be facile for both. Limitations of these reagents include the frequent need for (super)stoichiometric loading and the intrinsically poor atom economy that results from the generation of stoichiometric iodoarene by-products. In addition, hypervalent iodine reagents are often synthesized using metal-based terminal oxidants, which compound the resulting waste stream. Recently, substantial progress has been made to address these limitations. Here, we discuss progress toward sustainable synthetic methods for the preparation of hypervalent iodine compounds and the application of those methods in the context of hypervalent iodine catalysis. The discussion is organized according to the atom economy of the terminal oxidant employed. Hypervalent iodine electrochemistry and recyclable iodoarenes are discussed.
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