Advances in Transition-Metal-Catalyzed C–H Bond Oxygenation of Amides

Muniyappa Vijaykumar; Benudhar Punji

doi:10.1055/a-1481-2584

Synthesis, Inhaltsverzeichnis

Synthesis 2021; 53(17): 2935-2946
DOI: 10.1055/a-1481-2584

special topic

Bond Activation – in Honor of Prof. Shinji Murai

Advances in Transition-Metal-Catalyzed C–H Bond Oxygenation of Amides

Muniyappa Vijaykumar

^aOrganometallic Synthesis and Catalysis Lab, Chemical Engineering Division, CSIR–National Chemical Laboratory (CSIR–NCL), Dr. Homi Bhabha Road, Pune - 411 008, India

^bAcademy of Scientific and Innovative Research (AcSIR), Ghaziabad - 201 002, India

,

Benudhar Punji ∗

^aOrganometallic Synthesis and Catalysis Lab, Chemical Engineering Division, CSIR–National Chemical Laboratory (CSIR–NCL), Dr. Homi Bhabha Road, Pune - 411 008, India

^bAcademy of Scientific and Innovative Research (AcSIR), Ghaziabad - 201 002, India

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Abstract

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Abstract

C–O bond formation represents a fundamental chemical transformation in organic synthesis to develop valuably oxygenated (hetero)arenes. Particularly, the direct and regioselective C–H bond oxygenation of privileged amides, using a transition metal catalyst and a mild oxygenating source, is a step-economy and attractive approach. During the last decade, considerable progress has been realized in the direct C–H oxygenation of primary, secondary, and tertiary amides. This Short Review compiles the advances in transition-metal-catalyzed oxygenation of C(sp²)–H and C(sp³)–H bonds on various amides with diverse oxygenation sources. The review is categorized into two different major sections: (i) C(sp²)–H oxygenation and (ii) C(sp³)–H oxygenation. Each section is discussed based on the directing group (monodentate and bidentate) attached to the amide derivatives.

1 Introduction

2 C(sp²)–H Oxygenation

2.1 Monodentate Directed

2.2 Bidentate Directed

3 C(sp³)–H Oxygenation

3.1 Monodentate Directed

3.2 Bidentate Directed

4 Conclusion and Outlook

Key words

amides - C–H activation - directing group - oxygenation - transition metal

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