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

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

Publication History

Received: 30 April 2022

Accepted after revision: 04 August 2022

Accepted Manuscript online:
04 August 2022

Article published online:
06 October 2022

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