Direct Synthesis of α-Iodoenones by IPy₂BF₄-Promoted Rearrangement of Propargylic Esters

Tatiana Suárez-Rodríguez, Ángel L. Suárez-Sobrino, Alfredo Ballesteros*

*Instituto Universitario de Química Organometálica "Enrique Moles" and Departamento de Química Orgánica e Inorgánica, Universidad de Oviedo, c/Julián Clavería 8, Oviedo 33006, Spain, Email: abguniovi.es

T. Suárez-Rodríguez, Á. L. Suárez-Sobrino, A. Ballesteros, J. Org. Chem., 2018, 83, 12575-12583.

DOI: 10.1021/acs.joc.8b01746

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Abstract

Bis(pyridine) iodonium tetrafluoroborate (Barluenga's reagent) promotes the rearrangement of propargylic alcohol derivatives under mild conditions to provide β-unsubstituted, β-monosubstituted, and β,β-disubstituted α-iodoenones in high yields. β-Substituted α-iodoenones are obtained with excellent (Z)-selectivity.

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Key Words

vinyl iodides, enones, hypervalent iodine compounds

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ID: J42-Y2018