Synfacts 2009(12): 1342-1342  
DOI: 10.1055/s-0029-1218180
Synthesis of Materials and Unnatural Products
© Georg Thieme Verlag Stuttgart ˙ New York

Iodonium Ion Triggered Arene Functionalization

Contributor(s): Timothy M. Swager, Jason R. Cox
J. Barluenga*, E. Campos-Gómez, A. Minatti, D. Rodríguez, J. M. González
Unidad Asociada al C.S.I.C., Oviedo, Spain
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20. November 2009 (online)


This paper describes the inter- and intramolecular iodoallylation of arenes using an electrophilic iodine source as the trigger for the reaction. The intramolecular reaction proceeds under mild conditions and affords good yields of the iodoallylated product. These products can be further elaborated using cross-coupling chemistry to afford targets of increasing molecular complexity. The intermolecular variant provides smaller yields, but allows access to highly substituted olefins that are otherwise difficult to synthesize.