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Iodine(III)-Promoted Synthesis of Oxazoles through Oxidative Cyclization of N-Styrylbenzamides

Christian Hempel, Boris J. Nachtsheim*

*Institut für Organische Chemie, Eberhard Karls Universität, Auf der Morgenstelle 18, 72076 Tübingen, Germany, Email: boris.nachtsheimuni-tuebingen.de

C. Hempel, B. J. Nachtsheim, Synlett, 2013, 24, 2119-2123.

DOI: 10.1055/s-0033-1339491 (free Supporting Information)


Abstract

The hypervalent iodine reagent PhI(OTf)2, generated in situ, has been successfully utilized in a metal-free intramolecular oxidative cyclization of N-styrylbenzamides. In remarkably short reaction times, the desired 2,5-disubstituted oxazoles were isolated in high yields.

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Key Words

PIFA, umpolung, oxazoles, cyclization, heterocycles


ID: J60-Y2013