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Updated: Jul 3, 2026

Synthesis of Hypervalent Iodonium Alkynyl Triflates for the Application of Generating Cyanocarbenes
Published on: September 8, 2013
Synthesis of Iodinated Semisaturated Heterobicycles via a Temporal Dual Metal-Catalyzed Cycloaddition/Photochemical
Philip Samokhin1, Arthur Flaget1, Julian K Fernback1
1Department of Chemistry, University of Toronto, Lash Miller Chemical Laboratories, 80 St. George St., Toronto, Ontario M5S 3H6, Canada.
Abstract:
A dual-catalytic approach for the regioselective synthesis of iodinated semisaturated fused heterobicycles is reported. The one-pot sequential use of copper and palladium under blue-light irradiation enables the efficient synthesis of 1,2,3-triazole-fused piperidines in high yields from acyclic precursors, avoiding the need for highly reactive small-ring alkynes. Medicinally relevant compounds and functionally diverse product derivatives are described. The cooperativity between two independent bond-forming cycles is explored, and mechanistic studies of the photochemical palladium-catalyzed carboiodination suggest that cyclization is light-dependent.
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