Ph₃P/I₂-Catalyzed Beckmann Rearrangement of Ketoximes into Amides

Abstract

A Beckmann rearrangement of ketoximes reaction using triphenylphosphine/iodine as an effective catalyst in acetonitrile at reflux temperature is reported. The results indicate that conversion of oximes to amides can be reached in good to excellent yields under optimal reaction conditions within several minutes. The reaction mechanism is also proposed. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications to view the free supplemental file.

GRAPHICAL ABSTRACT

Keywords:

• Amide
• Beckman rearrangement
• iodine
• ketoximes
• triphenylphosphine

ACKNOWLEDGMENTS

This work was financially supported by the National Natural Science Foundation of China (20872085) and the Natural Science Foundation of Shaanxi Province (No. SJ08B22).

Notes

^a Isolated yields.

^a In CH₃CN, reflux, 10 mol% Ph₃P and 10 mol% I₂ as catalyst.

^b Isolated yields.