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DOI: 10.1055/a-1918-4191
Unlocking Electrophilic N-Aryl Intermediates from Aryl Azides, Nitroarenes, and Aryl Amines in Cyclization–Migration Reactions
The University of Illinois at Chicago, the ACS Petroleum Research Fund (46850-G1, 51853-ND7), the National Institute of General Medical Sciences (NIGMS) (R01GM084945, R01GM138388), and the National Science Foundation (CHE-1265630, CHE-1564959) are gratefully acknowledged for supporting our research program over the past 16 years.
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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
Publication History
Received: 01 July 2022
Accepted: 03 August 2022
Accepted Manuscript online:
05 August 2022
Article published online:
11 October 2022
© 2022. Thieme. All rights reserved
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For reports of decomposition products that are formed from the pyrolysis or photolysis of aryl azides, see:
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For recent reviews, see: