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Updated: Jan 29, 2026

Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
Published on: September 18, 2016
Unveiling the Potential of Nonactivated 1,3-Enynes for Controllable Divergent Gold-Catalyzed Cycloaddition with
Boris D Karagodin1, Dmitry V Dar'in1, Vadim Yu Kukushkin1,2
1Saint Petersburg State University, Universitetskaya Nab. 7/9, 199034 Saint Petersburg, Russian Federation.
None:
Nonactivated 1,3-enynes react with cyanamides under gold(I)-catalyzed conditions. This divergent interplay proceeds as [4 + 2]-bimolecular or [2 + 2 + 2]-trimolecular cycloadditions and affords 2-aminopyridines, 1-aminoisoquinolines, and 2,4-diaminopyrimidines. The impact of catalytic systems and electronic/steric parameters on reaction selectivity was studied, and these findings enable directing the cycloaddition along the desired pathway. As a result, a new highly selective modular approach to valuable 2-aminopyridines was proposed. The further synthetic potential of this methodology was demonstrated through postmodifications, including functionalizations of both the heterocyclic backbone and amino substituents.
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