Iodine-Catalyzed Nazarov Cyclizations

Jonas J. Koenig, Thiemo Arndt, Nora Gildemeister, Jörg-M. Neudörfl, Martin Breugst*

*Department of Chemistry, University of Cologne, Greinstraße 4, 50939 Köln, Germany, Email: mbreugstuni-koeln.de

J. J. Koenig, T. Arndt, N. Gildemeister, J.-M. Neudörfl, M. Breugst, J. Org. Chem., 2019, 84, 7587-7605.

DOI: 10.1021/acs.joc.9b01083

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Abstract

The Nazarov reaction can be performed under mild, metal-free reaction conditions using molecular iodine as the catalyst. Various divinyl ketones including aromatic systems undergo the I₂-catalyzed reaction with good yields. Addition of iodine to the double bond or a putative iodine-catalyzed cis-trans isomerization seem not to be important side reactions here.

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Key Words

Nazarov cyclization, cyclopentenones

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ID: J42-Y2019