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DOI: 10.1055/s-0030-1260237
The Oxidation of Amides to Imides: A Powerful Synthetic Transformation
Publication History
Publication Date:
27 September 2011 (online)
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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
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