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Title: Sustainable Methods in Hypervalent Iodine Chemistry
Hypervalent iodine compounds are a widely used class of metal-free oxidants that find application in organic synthesis. Due to the homology between the reactivity of hypervalent iodine and many transition metals ¾ oxidative addition, ligand exchange, and reductive elimination can be facile for both ¾ hypervalent iodine species find application in a variety of synthetically important organic transformations. Major 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 quantities of iodoarene byproducts. 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 towards sustainable synthetic methods for the preparation of hypervalent iodine compounds and application of those methods in the context of hypervalent iodine catalysis. The discussion is organized according to the active oxygen content, and thus atom economy, of the terminal oxidant employed. Hypervalent iodine electrochemistry and the development of recyclable iodoarenes are also discussed.  more » « less
Award ID(s):
1848135
NSF-PAR ID:
10232584
Author(s) / Creator(s):
; ; ; ;
Editor(s):
Muniz, K.; Ishihara, K.
Date Published:
Journal Name:
Organic synthesis
ISSN:
1047-773X
Format(s):
Medium: X
Sponsoring Org:
National Science Foundation
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