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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.

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


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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