A direct route into fused imidazo-diazines and imidazo-pyridines using nucleophilic nitrenoids in a gold-catalyzed formal [3 + 2]-dipolar cycloaddition

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Pyridinium N-(heteroaryl)aminides can be employed as robust and practical synthetic equivalents of nucleophilic 1,3-N,N-dipoles in a formal cycloaddition onto electron-rich alkynes under gold catalysis. Convergent and regioselective access to five types of imidazo-fused heteroaromatics is provided from the appropriate aminide. The efficient transformation accommodates significant structural variation around the aminide, ynamide, or indolyl-alkyne reactants and tolerates sensitive functional groups.


Original languageEnglish
Pages (from-to)4850-3
Number of pages4
JournalOrganic Letters
Issue number18
Publication statusPublished - 19 Sep 2014