Iodobenzene Diacetate - Efficient Terminal Oxidant for Transition-Metal-Mediated Transformations

Introduction

The most important use of hypervalent iodine compounds is as oxidizing agents replacing many other toxic reagents, usually based on heavy metals. Also, it has been observed that the synthetic properties of trivalent iodine compounds are often similar to those of lead and thallium derivatives, somehow with better yields and improved toxicity. The iodobenzene diacetate (most used acronyms are DIB or PIDA), a trivalent iodine derivative, which presents itself as white crystalline powder, is a prominent member. It has found multiple applications in organic chemistry as efficient and inexpensive reagent. [¹] Recently, its ability to act as terminal oxidant in palladium-, gold- or copper-­mediated transformations was disclosed and subsequently demonstrated. DIB is commercially available and can also be easily prepared by oxidation of iodobenzene with hydrogen peroxide urea complex in the presence of acetic anhydride, [²a] peracetic acid, [²b] or sodium perborate [¹a] (Scheme  [¹] ).

Scheme 1

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