Iodine-Based Reagents in Oxidative Amination and Oxygenation

Abstract

In this Account, we provide an overview of our recent advances in oxidative transformations that enable the introduction of nitrogen and oxygen functionalities into organic molecules by taking advantage of the unique characteristics of iodine-based reagents, such as hypervalency, soft Lewis acidity, high leaving ability, and radical reactivity. We also report on the development of new types of hypervalent iodine reagents containing a transferable nitrogen functional group with the objective of preparing primary amines, which is described in the latter part of this Account.

1 Introduction

2 Decarboxylative Functionalization of β,γ-Unsaturated Carboxylic Acids

3 Decarboxylative Functionalization at Tertiary Carbon Centers

4 C–H Bond Functionalization at Tertiary Carbon Centers

5 Intramolecular C–H Amination of Sulfamate Esters and N-Alkylsulfamides

6 Oxidative Amination with Hypervalent Iodine Reagents Containing Transferable Nitrogen Functional Groups

7 Summary and Outlook

Key words

iodine - hypervalent iodine - amination - oxygenation - oxidation - radical reaction

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