Abstract
Despite appearing to be a conceptually simple transformation,
the oxidation of amides to imides is far from straightforward, primarily
due to the inertness of amides toward electrophilic oxidants. This
perspective provides an overview of the development of reaction
conditions capable of effecting this oxidation. The application
of amide to imide oxidations in the fields of medicinal chemistry
and natural product synthesis, as well as the advantages and limitations
of the various oxidation conditions, is also discussed.
1 Introduction
2 Oxidation Methods
2.1 Ruthenium Tetroxide
2.2 Persulfates, Peroxides and Peracids
2.3 Aerobic Oxidation
2.4 Electrochemical Oxidation
2.5 Chromium Reagents
2.6 Hypervalent Iodine Reagents
2.7 Selectfluor-Copper Bromide
3 Conclusions
Key words
imide - amide - oxidation - organic
synthesis
