With a FeSO(4)/TBHP system in water, direct oxidation of sp(3) C-H bonds adjacent to nitrogen of arylureas to give both unprecedented tert-butoxylated and hydroxylated products 2 was revealed. Under elevated temperatures, either 2-oxo-N-arylpyrrolidine-1-carboxamides 3 or 1,3-diarylureas 4 were attained, depending on the aliphatic ring size of the arylurea substrates.

This study demonstrates the direct oxidation of arylureas with tert-butyl hydroperoxide to produce unprecedented tert-butoxylated and hydroxylated products, depending on the arylurea substrate's aliphatic ring size.

Paper

Iron(II)-catalyzed oxidation of sp3 C-H bonds adjacent to a nitrogen atom of unprotected arylureas with tert-butyl hydroperoxide in water.

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