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General Entry into o ‐, o′ ‐Heteroatom‐Linked N ‐(Hetero)aryl‐Imidazole Motifs by Gold‐Catalysed Formal [3+2]‐Dipolar Cycloaddition
Author(s) -
Garzón Miguel,
Arce Elsa M.,
Reddy Raju Jannapu,
Davies Paul W.
Publication year - 2017
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201700249
Subject(s) - chemistry , heteroatom , pyridinium , aryl , imidazole , cycloaddition , combinatorial chemistry , redox , stereochemistry , medicinal chemistry , organic chemistry , catalysis , ring (chemistry) , alkyl
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.