Recent Strategies in Non-Heme-Type Metal Complex-Catalyzed Site-, Chemo-, and Enantioselective C–H Oxygenations

Abstract

C–H bonds are ubiquitous and abundant in organic molecules. If such C–H bonds can be converted into the desired functional groups in a site-, chemo-, diastereo-, and enantio-selective manner, the functionalization of C–H bonds would be an efficient tool for step-, atom- and redox-economic organic synthesis. C–H oxidation, as a typical C–H functionalization, affords hydroxy and carbonyl groups, which are key functional groups in organic synthesis and biological chemistry, directly. Recently, significant developments have been made using non-heme-type transition-metal catalysts. Oxygen functional groups can be introduced to not only simple hydrocarbons but also complex natural products. In this paper, recent developments over the last fourteen years in non-heme-type complex-catalyzed C–H oxidations are reviewed.

1 Introduction

2 Regio- and Chemo-Selective C–H Oxidations

2.1 Tertiary Site-Selective C–H Oxidations

2.2 Secondary Site-Selective C–H Oxidations

2.3 C–H Oxidations of N-Containing Molecules

2.4 C–H Oxidations of Carboxylic Acids

2.5 Chemo- and Site-Selective Methylenic C–H Hydroxylations

3 Enantioselective C–H Oxidations

3.1 Desymmetrizations through C–H Oxidations

3.2 Enantiotopic Methylenic C–H Oxygenations

4 Conclusion

Key words

C–H oxidation - non-heme-type catalyst - site-selectivity - chemoselectivity - enantioselectivity - oxygen atom transfer

Publication History

Received: 29 April 2021

Accepted after revision: 09 June 2021

Accepted Manuscript online:
09 June 2021

Article published online:
12 July 2021

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