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