No transition metals are necessary to convert benzoxazoles and 1,3,4-oxadiazoles into the corresponding pharmacologically interesting 2-aminated heterocycles by formal direct C(2)-amination using tetramethylpiperidine-N-oxoammonium tetrafluoroborate (TEMPO+BF4−) as an oxidant (see scheme; TEMP=2,2,6,6-tetramethylpiperidine; TfOH=trifluoromethanesulfonic acid).
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Wertz et al. (2011) studied this question.
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