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

• to synthesize 1-carbamoyl-2-oxopropyl acetate derivatives by using (diacetoxyiodo)benzene (DIB) (Scheme 1) [31]. During the course of conditional optimization to synthesize 1-carbamoyl-2-oxopropyl acetate derivatives, we surprisingly found that almost none of the desired acetoxylation product was

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

• : 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

• cleavage along with the nucleophilic attack of the acetate ion on the C–N or C–C double bond of the intermediate 4, 5 or 6 affords the final product 2a. Conclusion In conclusion, we have shown an efficient and operationally simple method to synthesize 1-carbamoyl-2-oxopropyl acetate derivatives. The

• Wei-Bing Liu Cui Chen Qing Zhang Zhi-Bo Zhu School of Chemistry and Life Science, Guangdong University of Petrochemical Technology, Maoming 525000, China College of Pharmaceutical Sciences, Southern Medical University, Guangzhou 510515, China 10.3762/bjoc.7.167 Abstract 1-Carbamoyl-2-oxopropyl