Abstract
N-acyliminium ions are useful reactive synthetic intermediates in a variety of important carbon–carbon bond forming and cyclisation strategies in organic chemistry. The advent of an electrochemical anodic oxidation of unfunctionalised amides, more commonly known as the Shono oxidation, has provided a complementary route to the C–H activation of low reactivity intermediates. In this article, containing over 100 references, we highlight the development of the Shono-type oxidations from the original direct electrolysis methods, to the use of electroauxiliaries before arriving at indirect electrolysis methodologies. We also highlight new technologies and techniques applied to this area of electrosynthesis. We conclude with the use of this electrosynthetic approach to challenging syntheses of natural products and other complex structures for biological evaluation discussing recent technological developments in electroorganic techniques and future directions.
Highlights
Of electroorganic synthesis and the reader is directed to these articles for a thorough background and insight into the many facets of electrosynthesis [5,6,7,8,9,10]
We focus upon the development and application of the Shono-type electrochemical oxidation of unfunctionalised amides
The anodic oxidation/alkoxylation of amides pre-dates this work [12,13], Shono showed the synthetic utility of combining an electroorganic step with key carbon–carbon bond forming reactions required in synthetic organic chemistry
Summary
Received: 06 November 2014 Accepted: 05 December 2014 Published: 18 December 2014. This article is part of the Thematic Series "Electrosynthesis".
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