Copper-catalyzed domino synthesis of ynamines

The hitherto unexplored N -alkynylation of electron-withdrawing or protecting group free N-heteroarenes such as indole, carbazole and pyrrole was developed using gem -dibromoalkenes to synthesize ynamines under ligand-free copper-catalyzed domino conditions. The development methodology of ynamines w...

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Veröffentlicht in:Organic & biomolecular chemistry 2021-09, Vol.19 (36), p.7855-786
Hauptverfasser: Rao, Maddali L. N, Islam, Sk Shamim, Dasgupta, Priyabrata
Format: Artikel
Sprache:eng
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Zusammenfassung:The hitherto unexplored N -alkynylation of electron-withdrawing or protecting group free N-heteroarenes such as indole, carbazole and pyrrole was developed using gem -dibromoalkenes to synthesize ynamines under ligand-free copper-catalyzed domino conditions. The development methodology of ynamines was also applied in the synthesis of enynamines, multi-coupled bis-ynamines, tris-ynamines, and the natural product peyonine, demonstrating its broad synthetic scope and applications. A Cu-catalyzed domino protocol using gem -dibromoalkenes and N-heteroarenes is developed for the synthesis of ynamines and it is applied in the synthesis of enynamines, bis/tris-ynamines and peyonine natural product.
ISSN:1477-0520
1477-0539
DOI:10.1039/d1ob01383a