Hypervalent Iodine Chemistry by Thomas Wirth

Author:Thomas Wirth
Language: eng
Format: epub
Publisher: Springer International Publishing, Cham

5 Outlook

With the development of efficient synthetic routes to diaryliodonium salts, these hypervalent iodine compounds have become easily available and interesting alternatives to other arylation reagents. Their low toxicity, high stability, and high reactivity are attractive features which enable difficult transformations without the need for excess reagents or high temperatures. This chapter has summarized recent developments in metal-free and metal-catalyzed arylations of heteroatom nucleophiles and carbon-centered nucleophiles. The boundaries of the field have moved forward considerably in the last decade, and many more applications are foreseen based on the deepened mechanistic understanding of arylations under both metal-free and metal-catalyzed conditions.

Despite major achievements in this area, there are still several limitations to address. The formation of stoichiometric amounts of iodoarene make large-scale applications less appealing, and advancements in the area of solid-supported diaryliodonium salts would be of importance to simplify recovery of the iodoarene and avoid product purification problems. At present, such approaches are limited by time-consuming synthesis of the reagents, chemoselectivity problems, and/or moderate arylation yields. The development of reactions catalytic in diaryliodonium salt would be a major breakthrough with industrial relevance. Asymmetric arylations under metal-free conditions have proved to be very difficult to achieve, and further developments in this area are foreseen.

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