Azidation with Hypervalent Iodine Reagents

Dedicated to Prof. Cristina Nevado at the occasion of the awarding of the Dr. Margaret Faul Women in Chemistry Award 2021

Abstract

In this short review, we describe applications of hypervalent iodine reagents for the azidation of organic compounds from seminal publications to the most recent reports. After reviewing selected examples of azidations based on the use of in situ formed unstable non-cyclic reagents, we focus in more detail on stable cyclic hypervalent iodine reagents. Important advances in the azidation of C–H bonds, alkenes, as well as other transformations are described. Rather than being comprehensive, we highlight selected key reports that, in our opinion, especially contributed to the advancement of research in the field.

1 Introduction

2 Non-Cyclic λ³-Iodanes

3 Heterocyclic λ³-Iodanes

3.1 Azidation of Aliphatic C–H Bonds

3.2 Azidation of Alkenes

3.3 Other Azidations

4 Conclusion and Outlook

Key words

azidation - hypervalent iodine reagents - metal catalysis - photocatalysis - nucleoazidation - cyclization

Publication History

Received: 21 September 2022

Accepted after revision: 24 October 2022

Accepted Manuscript online:
24 October 2022

Article published online:
23 November 2022

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This review also covers I(V) reagents, whereas we focus on I(III). For seminal examples of azidation using I(V) reagents, see:
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