Divergent C-H Insertion–Cyclization Cascades of N-Allyl Ynamides

Holly V. Adcock, Elli Chatzopoulou, Paul W. Davies

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Gold carbene reactivity patterns were accessed by ynamide insertion into a C(sp3)[BOND]H bond. A substantial increase in molecular complexity occurred through the cascade polycyclization of N-allyl ynamides to form fused nitrogen-heterocycle scaffolds. Exquisite selectivity was observed despite several competing pathways in an efficient gold-catalyzed synthesis of densely functionalized C(sp3)-rich polycycles and a copper-catalyzed synthesis of fused pyridine derivatives. The respective gold–keteniminium and ketenimine activation pathways have been explored through a structure–reactivity study, and isotopic labeling identified turnover-limiting C[BOND]H bond-cleavage in both processes.
Original languageEnglish
Pages (from-to)15525-15529
JournalAngewandte Chemie
Issue number51
Early online date30 Oct 2015
Publication statusPublished - 14 Dec 2015


  • Carbene
  • Cyclopropanierung
  • Gold
  • Inamide
  • Stickstoffheterocyclen


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