Silver-Catalyzed Cyclization of Propargylic Amides to Oxazolines

Silver-Catalyzed Cyclization of Propargylic Amides to Oxazolines

A ligand‐accelerated effect is observed in the cyclization of propargylic amides catalyzed by bis(pyridyl)silver(I) complexes, with an unexpected reversal of electronic demand to the analogous NH addition reaction. The catalyst was found to be effective for internal alkyne substrates, offering excl...

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Veröffentlicht in:Advanced synthesis & catalysis 2015-12, Vol.357 (18), p.3943-3948
Hauptverfasser: Wong, Valerie H. L., White, Andrew J. P., Hor, T. S. (Andy), Hii, King Kuok (Mimi)
Format: Artikel
Sprache:eng
Schlagworte:
Alkynes
Amides
Catalysis
Catalysts
Chemical reactions
cyclization
Electronics
heterocycles
oxazolines
Selectivity
silver
Synthesis
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Zusammenfassung:A ligand‐accelerated effect is observed in the cyclization of propargylic amides catalyzed by bis(pyridyl)silver(I) complexes, with an unexpected reversal of electronic demand to the analogous NH addition reaction. The catalyst was found to be effective for internal alkyne substrates, offering exclusive selectivity for the 5‐exo‐dig product. Differences in selectivity profile between gold‐ and silver‐catalyzed processes are highlighted and discussed.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.201500610