Metal-Catalyzed C–H Bond Oxidation in the Total Synthesis of Natural and Unnatural Products
Emílio C. de Lucca, Victor C. S. Santana, Milena Fernandes, Isadora Cappuccelli, Ana Carolina G. Richieri
Abstract
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