Copper-Catalyzed Oxidation of Alkenes and Heterocycles

Dedicated to Professor Guillermo M. Massanet on the occasion of his 70^th birthday

Abstract

A variety of copper species catalyze the allylic oxidation of olefins and the introduction of an ester group at the α-position of a heterocycle. Both transformations are closely related in terms of reaction conditions and radical species involved. This short review highlights the progress made in these two types of oxidations, emphasizing work that has occurred within the last fifteen years.

1 Introduction

2 General Overview of the Copper-Catalyzed Allylic Oxidation of Olefins

3 Mechanistic Considerations

4 Enantioselective Version of the Allylic Oxidation of Olefins

5 Other Landmarks of the Copper-Catalyzed Oxidation of Olefins

6 α-Oxidation of Heterocycles

7 Reactions in Heterogeneous Phase

8 Applications

9 Summary

Key words

allylic oxidation - α-acyloxylation - copper - Kharasch–Sosnovsky reaction - olefins - heterocycles

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