Metal-Catalyzed C–H Bond Oxidation in the Total Synthesis of Natural and Unnatural Products

Victor C. S. Santana; Milena C. V. Fernandes; Isadora Cappuccelli; Ana Carolina G. Richieri; Emilio C. de Lucca Jr

doi:10.1055/a-1918-4338

Synthesis, Table of Contents

Synthesis 2022; 54(24): 5337-5359
DOI: 10.1055/a-1918-4338

review

Metal-Catalyzed C–H Bond Oxidation in the Total Synthesis of Natural and Unnatural Products

Authors

Victor C. S. Santana
Milena C. V. Fernandes
Isadora Cappuccelli
Ana Carolina G. Richieri
Emilio C. de Lucca Jr ∗

Abstract

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Abstract

C–H bond oxidation is a powerful means for oxygen incorporation in organic molecules. Its use results in fast structural diversification and in a new way of thinking about retrosynthetic disconnections. In this review, we present the application of five metal-catalyzed methodologies for C(sp ³)–H oxidation in the total synthesis of natural and unnatural products, covering the period of 2004–2022.

1 Introduction

2 Copper-Mediated Hydroxylation of Methylenes β to Imines

3 Palladium Acetoxylation of Methyl Groups β to Oximes

4 Palladium-Mediated Allylic C–H Bond Oxidation of Terminal Olefins

5 Iron- and Manganese-Mediated Aliphatic Oxidation

6 Miscellaneous

7 Conclusion

Key words

C–H bond oxidation - catalysis - total synthesis - natural products - transition metals

Full Text

References

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