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Froehr T, Sindlinger CP, Kloeckner U, et al. A metal-free amination of benzoxazoles--the first example of an iodide-catalyzed oxidative amination of heteroarenes. Org Lett. 2011;13(14):3754-7doi: 10.1021/ol201439t.
Froehr, T., Sindlinger, C. P., Kloeckner, U., Finkbeiner, P., & Nachtsheim, B. J. (2011). A metal-free amination of benzoxazoles--the first example of an iodide-catalyzed oxidative amination of heteroarenes. Organic letters, 13(14), 3754-7. https://doi.org/10.1021/ol201439t
Froehr, Tanja, et al. "A metal-free amination of benzoxazoles--the first example of an iodide-catalyzed oxidative amination of heteroarenes." Organic letters vol. 13,14 (2011): 3754-7. doi: https://doi.org/10.1021/ol201439t
Froehr T, Sindlinger CP, Kloeckner U, Finkbeiner P, Nachtsheim BJ. A metal-free amination of benzoxazoles--the first example of an iodide-catalyzed oxidative amination of heteroarenes. Org Lett. 2011 Jul 15;13(14):3754-7. doi: 10.1021/ol201439t. Epub 2011 Jun 21. PMID: 21688859.
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Org Lett. 2011 Jul 15;13(14):3754-7. doi: 10.1021/ol201439t. Epub 2011 Jun 21.

A metal-free amination of benzoxazoles--the first example of an iodide-catalyzed oxidative amination of heteroarenes.

Organic letters

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

Affiliations

  1. Institut für Organische Chemie, Eberhard Karls Universität Tübingen, Auf der Morgenstelle 18, 72076 Tübingen, Germany.

PMID: 21688859 DOI: 10.1021/ol201439t

Abstract

An efficient transition-metal-free amination of benzoxazoles has been developed. With catalytic amounts of tetrabutylammoniumiodide (TBAI), aqueous solutions of H(2)O(2) or TBHP as co-oxidant and under mild reaction conditions, highly desirable 2-aminobenzoxazoles were isolated in excellent yields of up to 93%. First mechanistic experiments indicate the in situ iodination of the secondary amine as the putative mode of activation.

© 2011 American Chemical Society

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