Synthesis 2011(22): 3569-3580  
DOI: 10.1055/s-0030-1260237
REVIEW
© Georg Thieme Verlag Stuttgart ˙ New York

The Oxidation of Amides to Imides: A Powerful Synthetic Transformation

Jonathan Sperry*
School of Chemical Sciences, University of Auckland, 23 Symonds Street, Auckland, New Zealand
e-Mail: j.sperry@auckland.ac.nz.;
Weitere Informationen

Publikationsverlauf

Received 1 August 2011
Publikationsdatum:
27. September 2011 (online)

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