Synthesis 2016; 48(15): 2323-2342
DOI: 10.1055/s-0035-1561649
short review
© Georg Thieme Verlag Stuttgart · New York

Copper-Catalyzed Oxidation of Alkenes and Heterocycles

Ana Leticia García-Cabeza
a  Departamento de Química Orgánica, Facultad de Ciencias, Universidad de Cádiz, Polígono Río San Pedro s/n. 11510 Puerto Real, Cádiz, Spain
,
F. Javier Moreno-Dorado
a  Departamento de Química Orgánica, Facultad de Ciencias, Universidad de Cádiz, Polígono Río San Pedro s/n. 11510 Puerto Real, Cádiz, Spain
,
María J. Ortega
b  Departamento de Química Orgánica, Facultad de Ciencias del Mar y Ambientales, Universidad de Cádiz, Polígono Río San Pedro s/n. 11510 Puerto Real, Cádiz, Spain   Email: [email protected]
,
Francisco M. Guerra*
a  Departamento de Química Orgánica, Facultad de Ciencias, Universidad de Cádiz, Polígono Río San Pedro s/n. 11510 Puerto Real, Cádiz, Spain
› Author Affiliations
Further Information

Publication History

Received: 04 April 2016

Accepted: 18 April 2016

Publication Date:
15 June 2016 (online)


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

 
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