Organic synthesis using (diacetoxyiodo)benzene (DIB): Unexpected and novel oxidation of 3-oxo-butanamides to 2,2-dihalo-N-phenylacetamides

• Wei-Bing Liu,
• Cui Chen,
• Qing Zhang and
• Zhi-Bo Zhu

Beilstein J. Org. Chem. 2012, 8, 344–348, doi:10.3762/bjoc.8.38

• chemical synthesis. This protocol not only adds a new aspect to reactions that use other hypervalent iodine reagents but also provides a wide space for the synthesis of disubstituted acetamides. Keywords: cleavage of carbon–carbon bond; (diacetoxyiodo)benzene; difunctionalized acetamides; novel oxidation

• application of this protocol to synthesize difunctionalized acetamides from 3-oxo-butanamides is reported here for the first time. In order to probe the mechanism of this transformation, we employed 2,2-dichloro-3-oxo-N-phenylbutanamide (1m) and 2,2-dibromo-3-oxo-N-phenylbutanamide (1n) as reactants under

• to the synthesis of other difunctionalized acetamides and detailed investigations of the reaction mechanism are in progress. Synthesis of 1-carbamoyl-2-oxopropyl acetates. Synthesis of 2,2-dihalo-N-phenylacetamides. Synthesis of dichloroacetamides. Reagents and conditions: 1 (1.0 mmol), dioxane (2 mL