Cu-Catalyzed Cascades to Carbocycles: Union of Diaryliodonium Salts with Alkenes or Alkynes Exploiting Remote Carbocations

Fengzhi Zhang, Shoubhik Das, Andrew J. Walkinshaw, Alicia Casitas, Michael T. Taylor, Marcos G. Suero, Matthew J. Gaunt

Journal of the American Chemical Society · 2014 · 154 citations · 27 references

Concepts

Abstract

Copper-catalyzed cascade reactions between alkenes or alkynes and diaryliodonium salts form carbocyclic products in a single step. Arylation of the unsaturated functional group is proposed to form a carbocation intermediate that facilitates hydride shift pathways to translocate the positive charge to a remote position and enables ring formation via a Friedel-Crafts-type reaction.

References

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