A Versatile and Highly Reactive Polyfluorinated Hypervalent Iodine(III) Compound

摘要

Hypervalent iodine compounds are frequently used reagents that have found wide application in synthesis. They are used in a wide range of transformations as environmentally friendly, mild, and highly selective electrophilic reagents and oxidants since their application sidesteps the issues of toxicity and the complicated ligands of many transition-metal-based systems commonly used for such processes. The drawback of hypervalent iodine compounds can be their low solubility in commonly used organic solvents as well as their potentially explosive character (sometimes found for hyperveralent iodine(V) compounds). Commonly used hypervalent iodine(III) compounds such as PhI(OAc)2 and PhI(OCOCF3)2 have only moderate reactivity owing to their lower oxidation state. Because polyfluorinated alkyl-substituted hypervalent iodine compounds and C6F5I(OCOCF3)2 show increased reactivity and solubility and are easy to recycle, we recently introduced tetrafluorinated IBA (5,6,7,8-tetrafluoro-1-hydroxybenz-iodoxol-3-one) and IBX (5,6,7,8-tetrafluoro-1-hydroxy-1-oxobenziodoxol-3-one) derivatives.