The Shono-type Electroorganic Oxidation of Unfunctionalised Amides. Carbon-carbon Bond Formation Via Electrogenerated N-acyliminium Ions

Overview

Journal Beilstein J Org Chem

Specialty Chemistry

Date 2015 Feb 12

PMID 25670975

Citations 23

Authors

Alan M Jones

Craig E Banks

Affiliations

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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.

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