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

…, U Kloeckner, P Finkbeiner, BJ Nachtsheim

Index: Froehr, Tanja; Sindlinger, Christian P.; Kloeckner, Ulrich; Finkbeiner, Peter; Nachtsheim, Boris J. Organic Letters, 2011 , vol. 13, # 14 p. 3754 - 3757

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Citation Number: 174

Abstract

An efficient transition-metal-free amination of benzoxazoles has been developed. With catalytic amounts of tetrabutylammoniumiodide (TBAI), aqueous solutions of H2O2 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.