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Synthesis 2021; 53(18): 3235-3246
DOI: 10.1055/a-1525-4335
DOI: 10.1055/a-1525-4335
special topic
Bond Activation – in Honor of Prof. Shinji Murai
Recent Strategies in Non-Heme-Type Metal Complex-Catalyzed Site-, Chemo-, and Enantioselective C–H Oxygenations
Financial support from the International Institute for Carbon-Neutral Energy Research (WPI-I2CNER) from MEXT, Japan, is gratefully acknowledged.
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 transferPublikationsverlauf
Eingereicht: 29. April 2021
Angenommen nach Revision: 09. Juni 2021
Accepted Manuscript online:
09. Juni 2021
Artikel online veröffentlicht:
12. Juli 2021
© 2021. Thieme. All rights reserved
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