Unlocking Electrophilic N-Aryl Intermediates from Aryl Azides, Nitroarenes, and Aryl Amines in Cyclization–Migration Reactions

Tom G. Driver

doi:10.1055/a-1918-4191

Synlett, Table of Contents

Synlett 2022; 33(19): 1890-1901
DOI: 10.1055/a-1918-4191

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Unlocking Electrophilic N-Aryl Intermediates from Aryl Azides, Nitroarenes, and Aryl Amines in Cyclization–Migration Reactions

Tom G. Driver ∗

Abstract

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Dedicated to Driver group members past, present, and future.

Abstract

An account of our development of reactions to construct N-heterocycles by triggering cyclization–migration tandem reactions from aryl azides, nitroarenes, and aryl amines is described. The reactivity patterns of metal N-aryl nitrenes, nitrosoarenes, N-aryl nitrogen radical anions, and N-aryl nitrenoids are compared.

1 Introduction

2 Unlocking the Reactivity Embedded in Aryl Azides

3 Exploiting the Reactivity of Nitrosoarenes Generated from Nitroarenes

4 Radical Anion N-Aryl Nitrogen Reactive Intermediates from Nitroarenes

5 Oxidation of Aryl Amines to Access Electrophilic N-Aryl Nitrenoids

6 Conclusion

Key words

azides - N-heterocycles - nitroarenes - nitrene - nitrosoarene

Full Text

References

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