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

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 beta to Imines 3 Palladium Acetoxylation of Methyl Groups beta to Oximes 4 Palladium-Mediated Allylic C-H Bond Oxidation of Terminal Olefins 5 Iron- and Manganese-Mediated Aliphatic Oxidation 6 Miscellaneous 7 Conclusion

Automated summary

C-H bond oxidation is a powerful tool for introducing oxygen atoms into organic molecules and provides a new perspective on retrosynthetic disconnections. This review summarizes the application of five metal-catalyzed methodologies for C(sp(3))-H oxidation in the total synthesis of natural and unnatural products.