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

Victor C. S. Santana
,
Milena C. V. Fernandes
,
Isadora Cappuccelli
,
Ana Carolina G. Richieri
,
We are grateful to São Paulo Research Foundation (FAPESP) for the financial support for this work (grant 2018/04837-6) and fellowships to V. C. S. Santana and M. C. V. Fernandes (grants 2019/27528-1 and 2021/07167-4). We also thank CNPq, CAPES, and FAEPEX-UNICAMP (2575/21).


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



Publication History

Received: 30 April 2022

Accepted after revision: 04 August 2022

Accepted Manuscript online:
04 August 2022

Article published online:
06 October 2022

© 2022. Thieme. All rights reserved

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany

 
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