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A Predictably Selective Palladium-Catalyzed Aliphatic C-H Oxygenation.

Dmitry P Lubov^1,2, Mikhail V Shashkov¹, Andrey A Nefedov^2,3

¹Boreskov Institute of Catalysis, Pr. Lavrentieva 5, Novosibirsk 630090, Russian Federation.

Organic Letters

|February 24, 2023

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This study introduces a novel palladium catalyst for direct oxygenation of C-H bonds using peroxycarboxylic acids. The method achieves high yields and stereospecificity, enabling selective functionalization of complex molecules.

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Area of Science:

Organic Chemistry
Catalysis
Synthetic Methodology

Background:

Direct functionalization of nonactivated C(sp³)-H bonds remains a significant challenge in organic synthesis.
Developing selective and efficient oxidation methods is crucial for accessing diverse chemical structures.
Palladium catalysis offers promising avenues for C-H activation and functionalization.

Purpose of the Study:

To report a novel catalytic system for direct oxygenation of aliphatic C(sp³)-H groups.
To investigate the stereospecificity and regioselectivity of the developed oxidation reaction.
To explore the potential applications of this method in the functionalization of complex molecules.

Main Methods:

Direct oxygenation of nonactivated aliphatic C(sp³)-H bonds using peroxycarboxylic acids.
Employing a palladium tris(pyridylmethyl)amine complex as the catalyst (0.6 mol %).
Analysis of reaction yields, stereospecificity, and regioselectivity, including electronic effects.

Main Results:

Achieved up to 94% yields of hydroxylated derivatives from direct C-H oxygenation.
Demonstrated stereospecific oxidation of tertiary (3°) C-H groups.
Exhibited high regioselectivity, with 3°:2° C-H oxidation ratios exceeding 300 in adamantane oxidation, highlighting extreme sensitivity to electronic effects.

Conclusions:

The reported palladium-catalyzed system enables efficient and selective direct oxygenation of nonactivated C(sp³)-H bonds.
The reaction's high stereospecificity and regioselectivity offer precise control over functionalization.
This methodology holds significant potential for the 3°-regioselective oxidative functionalization of complex natural products and other valuable molecules.