General Entry into o‐,o′‐Heteroatom‐Linked N‐(Hetero)aryl‐Imidazole Motifs by Gold‐Catalysed Formal [3+2]‐Dipolar Cycloaddition

A general redox‐neutral approach into the o‐,o′‐heteroatom‐linked N‐(hetero)aryl‐imidazole family of heteroaromatics has been developed. New types of heteroatom substituted carbimidoyl nitrenoids are efficiently realised from robust, bench‐stable N‐(heteroaryl)‐pyridinium‐N‐aminides by formal gold‐c...

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Bibliographic Details
Published in:Advanced synthesis & catalysis 2017-06, Vol.359 (11), p.1837-1843
Main Authors: Garzón, Miguel, Arce, Elsa M., Reddy, Raju Jannapu, Davies, Paul W.
Format: Article
Language:English
Subjects:
Aromatic compounds
Cycloaddition
dipoles
Gold
Imidazole
nitrogen heterocycles
nucleophilic nitrenoids
Scaffolds
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Summary:A general redox‐neutral approach into the o‐,o′‐heteroatom‐linked N‐(hetero)aryl‐imidazole family of heteroaromatics has been developed. New types of heteroatom substituted carbimidoyl nitrenoids are efficiently realised from robust, bench‐stable N‐(heteroaryl)‐pyridinium‐N‐aminides by formal gold‐catalysed [3+2]‐dipolar cycloadditions across ynamides. Broad structural variety and functional group tolerance allows rapid access into diverse functionalised scaffolds, as exemplified by the preparation of 8 different heteroaromatic cores.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.201700249