Aerobic Oxidations via Organocatalysis: A Mechanistic Perspective

Yongtao Wang; Jia Yao; Haoran Li

doi:10.1055/a-1661-6124

Synthesis, Inhaltsverzeichnis

Synthesis 2022; 54(03): 535-544
DOI: 10.1055/a-1661-6124

short review

Aerobic Oxidations via Organocatalysis: A Mechanistic Perspective

Yongtao Wang

^aDepartment of Chemistry and ZJU-NHU United R&D Center, Zhejiang University, 38 Zheda Road, Hangzhou, 310027, P. R. China

^bCenter of Chemistry for Frontier Technologies, Zhejiang University, 38 Zheda Road, Hangzhou, P. R. China

,

Jia Yao

^aDepartment of Chemistry and ZJU-NHU United R&D Center, Zhejiang University, 38 Zheda Road, Hangzhou, 310027, P. R. China

,

Haoran Li∗

^aDepartment of Chemistry and ZJU-NHU United R&D Center, Zhejiang University, 38 Zheda Road, Hangzhou, 310027, P. R. China

^cState Key Laboratory of Chemical Engineering and College of Chemical and Biological Engineering, Zhejiang University, 38 Zheda Road, Hangzhou, P. R. China

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Abstract

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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 radical

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Referenzen

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