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

• ; 3-oxo-N-phenylbutanamides; Introduction Hypervalent iodine(III) reagents [1][2][3][4][5][6][7][8][9][10][11][12][13][14][15][16][17][18] have received much attention, as reflected by the plethora of publications and reviews [19][20][21][22][23]. This is due to their low toxicity, ready availability

• DIB (Table 1, entry 5). After optimizing the reaction conditions, we used a range of 3-oxo-N-phenylbutanamides to explore the substrate scope and limitations of this reaction. As shown in Scheme 3, all the reactions proceeded smoothly and gave the corresponding N-phenyl dichloroacetamides 2a–2k

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

• be the optimum amount of DIB (Table 1, entries 11–13). To explore the substrate scope and limitations of this reaction, a range of 3-oxo-N-phenylbutanamides were then examined under the optimized reaction conditions. The results are shown in Scheme 2. We found that the reaction led to the