Allylic Oxidations of Olefins to Enones

Abstract

Allylic oxidations of olefins to enones are C–H functionalizations and are valuable organic transformations that permit the synthesis of value-added products from simple precursors. A variety of stoichiometric and catalytic metal-based methods are available for these conversions. In addition, metal-free and biocatalytic protocols are gaining in importance. This review summarizes the available oxidation methods and compares their regio- and chemoselectivities.

1 Introduction

2 Chromium-Based Oxidation

2.1 Stoichiometric Methods

2.2 Catalytic Methods

2.3 Chromium on Solid Support

3 Regio- and Chemoselectivity of Allylic Oxidations

4 Other Metal-Based Oxidations

4.1 Copper Reagents

4.2 Rhodium Reagents

4.3 Selenium Reagents

4.4 Cobalt Reagents

4.5 Ruthenium Reagents

4.6 Palladium Reagents

4.7 Iron Reagents

4.8 Other Metal Reagents

5 Metal-Free and Biocatalytic Methods

5.1 Metal-Free Methods

5.2 Biocatalytic Methods

6 Conclusion

Key words

allylic oxidation - terpenoids - oxidation - C–H activation - steroids - alkenes - enones - catalysis

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