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
