Oxidative Rearrangements with Hypervalent Iodine Reagents

Abstract

Hypervalent iodine chemistry is used as an important tool in synthetic and natural product chemistry. A number of hypervalent iodine reagents can be used to generate the functionalizations on various scaffolds by several chemical approaches including oxidation reactions, oxidative cyclization reactions, and rearrangements. Recently, these reagents have been employed to develop a variety of oxidative rearrangements. In this review article, various aspects of recently developed oxidative rearrangements using iodine(III) and iodine(V) reagents are described.

1 Introduction

2 Oxidative Rearrangements

2.1 1,2-Aryl Group Migrations

2.2 Hofmann Rearrangements

2.2.1 Hofmann Rearrangements without Cyclizations

2.2.2 Hofmann Rearrangements with Cyclizations

2.3 Ring Contractions

2.4 Ring Expansions

2.5 Rearrangement of Tertiary Alcohols

2.6 Wagner–Meerwein Rearrangements

2.7 Domino Reactions

3 Summary

Key words

hypervalent iodine reagents - oxidative rearrangements - ring contractions - ring expansions

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