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Synthesis 2022; 54(03): 535-544
DOI: 10.1055/a-1661-6124
DOI: 10.1055/a-1661-6124
short review
Aerobic Oxidations via Organocatalysis: A Mechanistic Perspective
This work was supported by the Fundamental Research Funds for the Central Universities, and the National Natural Science Foundation of China (No. 22073081).
Abstract
This review focuses on recent advances and mechanistic views of aerobic C(sp3)–H oxidations catalyzed by organocatalysts, where metal catalysis and photocatalysis are not included.
1 Introduction
2 Carbanion Route: TBD-Catalyzed C(sp3)–H Oxygenation
2.1 α-Hydroxylation of Ketones
2.2 Carbonylation of Benzyl C(sp3)–H
3 Radical Route: NHPI-Catalyzed C(sp3)–H Oxidation
3.1 N-Oxyl Radicals and Mechanisms
3.2 Oxygenation of Benzyl C(sp3)–H
3.3 Solvent Effects
4 Hydride-Transfer Route: TEMPO-Catalyzed Oxidations
4.1 Oxoammonium Cation and Mechanisms
4.2 Dehydrogenation of Alcohols
4.3 Oxygenation of Benzyl C(sp3)–H
5 Conclusions and Outlook
Key words
organocatalysis - aerobic oxidation - C(sp3)–H bond - mechanism - hydrogen bond - guanidine - N-oxyl radicalPublication History
Received: 02 July 2021
Accepted after revision: 05 October 2021
Accepted Manuscript online:
05 October 2021
Article published online:
30 November 2021
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