A Metal-Free Amination of Benzoxazoles - The First Example of an Iodide-Catalyzed Oxidative Amination of Heteroarenes

Tanja Froehr, Christian P. Sindlinger, Ulrich Kloeckner, Peter Finkbeiner and Boris J. Nachtsheim*

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

T. Froehr, C. P. Sindlinger, U. Kloeckner, P. Finkbeiner, B. J. Nachtsheim, Org. Lett., 2011, 13, 3754-3757.

DOI: 10.1021/ol201439t

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Abstract

Catalytic amounts of tetrabutylammoniumiodide (TBAI), aqueous solutions of H₂O₂ or TBHP as co-oxidant enabled an efficient transition-metal-free amination of benzoxazoles under mild reaction conditions, to yield highly desirable 2-aminobenzoxazoles in good yields. First mechanistic experiments indicate the in situ iodination of the secondary amine as the putative mode of activation.

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Key Words

Benzoxazoles, TBHP

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ID: J54-Y2011-2060