Hypervalent iodine(III)-induced methylene acetoxylation of 3-oxo-N-substituted butanamides

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

Beilstein J. Org. Chem. 2011, 7, 1436–1440, doi:10.3762/bjoc.7.167

• acetate derivatives were synthesized through an acetoxylation process to methylene with the aid of (diacetoxyiodo)benzene (DIB) as the oxidant. Not only mild reaction conditions, but also excellent yields and good substrate scope make the present protocol potentially useful in organic synthesis. Keywords

• : 1-carbamoyl-2-oxopropyl acetate derivatives; C-hetero bond; (diacetoxyiodo)benzene; methylene acetoxylation; Introduction Carbon–carbon, carbon–heteroatom bond formation leading to useful molecular structures is one of the most interesting and challenging research topics in organic chemistry [1][2

• groups make these compounds valuable tools in organic synthesis [31][32][33][34][35][36]. Our interest in the chemistry of polyvalent iodine(III) reagents [37][38][39] prompted us to exploit the reactivity of (diacetoxyiodo)benzene (DIB). We report herein the use of DIB, as a nucleophile and oxidant, to